CN110088925A - Mixture comprising at least two organic functions chemical combination objects - Google Patents

Abstract

The present invention relates to comprising being each other the mixture of at least two organic functions chemical combination object OSM1 and OSM2 of constitutional isomer, especially it is used in electronic device.The invention further relates to the methods for being used to prepare compound according to the present invention, and the electronic device comprising the compound.

Description

Mixture comprising at least two organic functions chemical combination objects

The present invention describes the mixture comprising at least two organic functions chemical combination objects, in particular for electronic device In.The invention further relates to the methods for being used to prepare the inventive mixture comprising at least two organic functions chemical combination objects, and packet Electronic device containing these compounds.

Electronic device comprising organic, organic metal and/or polymer semiconductor becomes more and more important, and at This reason and it is used in many commercial products due to its performance.Here example includes in duplicator based on organic matter Charge transport materials (such as hole mobile material based on triarylamine) are read and the organic or polymer hair in display device Organophotoreceptorswith in optical diode (OLED or PLED) or duplicator.Organic solar batteries (O-SC), organic effect Transistor (O-FET), Organic Thin Film Transistors (O-TFT), organic integrated circuits (O-IC), organic image intensifer and organic laser Diode (O- laser) is in the advanced development phase and can have very big Future Significance.

These devices use the solution of organic functional material to prepare in many cases.However, since these materials are being permitted Solubility in more situations is relatively low, therefore using the highly concentrated or oversaturated solution relative to solubility limit, but It is that these solution have crystallization tendency in the case wheres small sample perturbations such as temperature change, mechanical stress etc..

So far, it is solved by using as the dissolution described in such as 2011/137922 A1 of WO improves group The problem.In addition, 2007/020485 A1 of document US 2003/031893 A1 and US discloses stereoisomer, but this It cannot lead to the satisfactory solution to the above problem a bit.

Known compound or composition for manufacturing electronic device have available performance characteristic.However, there is a continuing need for Improve the performance of these materials and device.

These performances especially include machinability, rodability and the storability for manufacturing the material of electronic device.

In addition, the service life of electronic device and its other performance should not be simultaneously at above-mentioned aspect by the unfavorable of material improvement It influences.These include the energy efficiency that electronic device solves bound problem.It can be based on low molecular weight compound or be based on polymerization In the case where the Organic Light Emitting Diode of object material, especially light output should be sufficiently high so that must apply the electricity of minimum Power is to realize specific luminous flux.In addition it is also necessary to which minimum voltage realizes restriction luminous density.

Another problem solved, which is considered, to be dirt cheap ground and has excellent properties with constant-quality offer Electronic device.

Many purposes are used in addition, electronic device can should be used for or be adjusted.More specifically, the performance of electronic device It should be maintained within the scope of wide in range temperature.

Another problem solved by the invention is to provide following material, it is suitable in organic electronic device, especially In organic electroluminescence device, and good device performance is generated when using in the device, and corresponding electricity is provided Sub- device.

More specifically, problem solved by the invention is to provide the change for leading to high life, good efficiencies and low-work voltage Close object.Especially the characteristic of host material also has great influence to the service life of organic electroluminescence device and efficiency.

Another problem solved by the invention, which may be considered that, to be to provide suitable for phosphorescence or fluorescence OLED, especially Compound as host material.A particular problem solved by the invention is to provide suitable for red, yellow and green phosphorus Light OLED and the host material that could be applicable to blue phosphorescent OLED.In addition, the fluorescence radiation with excellent characteristics should be provided Body.

In addition, the compound can should be processed in a very simplified manner, and especially show good dissolubility And film forming.For example, the compound should show raising oxidation stability and improved glass transition temperature.

Surprisingly, it has been found that the specific compound being described in detail below solves these problems and eliminates existing The shortcomings that technology.Mixture use especially can the machinability of the material for manufacturing electronic device, rodability and It realizes and improves in terms of storability.In this case, the use of mixture leads to organic electronic device, especially organic electroluminescence The extraordinary performance of luminescent device, especially situation is such in terms of service life, efficiency and operating voltage.Therefore, the present invention mentions The electronic device comprising this mixture and corresponding preferred embodiment, especially organic electroluminescence device are supplied.

Therefore, the present invention provides a kind of mixtures, and it includes the functional layers that at least two can be used for manufacturing electronic device Organic functions chemical combination object OSM1 and OSM2, it is characterised in that the compound OSM1 and OSM2 is mutual constitutional isomer.

Constitutional isomer is universal experience formula having the same but its construction, i.e. its structure is different, they are had There is the compound of different atomic series and/or different keys.Therefore, constitutional isomer is being fundamentally different from stereoisomer, institute Stating stereoisomer includes enantiomter and diastereoisomer.In many cases, constitutional isomer is divided into function isomery Body, skeletal isomer, position isomer and bonding isomer.In the case where function isomers and bonding isomer, describedization Different reactivity can be had by closing object；For example, ethyl alcohol includes hydroxyl group, and the dimethyl ether of stereo isomers has ether group.Bone Frame isomers and position isomer are different in the branching of functional group and/or position, so that these constitutional isomers can have base Identical degree of functionality in sheet.Therefore, statement " substantially the same degree of functionality " refer in possessive construction isomers all exist it is potential Functional group, i.e. such as hydroxyl group, phenyl ring or ester group, but do not consider these groups due to anti-caused by different substitutions It should sexually revise.For example, due to spatial chemistry, the reactivity of 1- n-butanol and the tert-butyl alcohol is there are measurable difference, but degree of functionality It itself is identical.However, in this regard, these the measurable differences covered by term " substantially the same degree of functionality " It will be ignored, because two kinds of compounds all have hydroxy functional group in this example.On the other hand, propine has an alkynes function Group, and there are two olefin functionalities for allene tool.Compared with alkynes, alkene has different functions in the context of the present invention Degree, because they for example show different acidity.Therefore, compared with allene, propine does not have " substantially the same function Degree ".

Preferred mixture include at least two organic functions chemical combination object OSM1 with substantially the same degree of functionality and OSM2.Accordingly, it is preferred that organic functions chemical combination object OSM1 and OSM2 are constitutional isomers, but not instead of function isomers, bone Frame isomers and/or position isomer.In another configuration of the invention, the mixture preferably includes at least three kinds, More preferably at least four kinds of functional compounds OSM1, OSM2, OSM3 and/or OSM4, wherein for comprising at least described in context Preferred embodiment described in the mixture of two kinds of organic functions chemical combination objects OSM1 and OSM2 is also correspondingly applied to comprising two kinds The mixture of the above organic functions chemical combination object.

Two kinds of organic functions chemical combination object OSM1 being present in this mixture for the functional layer that can be used for manufacturing electronic device Fluorescent illuminant, phosphorescent emitter, illuminator, the main body material for showing TADF (hot activation delayed fluorescence) are preferably selected from OSM2 Material, electron transport material, exciton-blocking material, electron injection material, hole conductor material, hole-injecting material, n-type doping Agent, p-type dopant, wide bandgap material, electron-blocking materials and/or hole barrier materials.

At least two organic functions chemical combination object OSM1 and OSM2 of inventive mixture preferably have the virtue of identical quantity Race or heteroaromatic ring system, the ring system respectively have 5 to 40 annular atoms, wherein the condensation level of the ring system is identical and institute It states ring system and has basically the same substituent group.

It is preferred that feasible situation is, at least two organic functions chemical combination the object OSM1 and OSM2 respectively have at least two Aromatics or heteroaromatic ring system, the ring system respectively have 5 to 40 annular atoms, wherein at least two organic functions chemical combination object OSM1 and OSM2 the difference is that, at least two aromatics or heteroaromatic rings tie up to different sites and are connected to each other.

In another arrangement, mixture of the invention may include at least two organic functions chemical combination object OSM1 and OSM2, It each is selected from phenyl, fluorenes, indenofluorene, two fluorenes of spiral shell, carbazole, indeno carbazole, indolocarbazole, spiral shell carbazole, pyrimidine, and triazine is interior Amide, triarylamine, dibenzofurans, dibenzothiophenes, imidazoles, benzimidazole, benzoAzoles, benzothiazole, 5- aryl are luxuriant and rich with fragrance Pyridine -6- ketone, 9,10- dehydrogenations are luxuriant and rich with fragrance, fluoranthene, anthracene, benzanthracene, indeno [1,2,3-jk] fluorenes (Fluoradene).

Preferably, the organic functions chemical combination object OSM1 may include at least one functional architecture unit and at least one substitution Base S1, and the organic functions chemical combination object OSM2 may include at least one functional architecture unit and at least one substituent group S2, The functional architecture unit that wherein organic functional closes the object OSM1 and organic functions chemical combination object OSM2 is identical.

Furthermore feasible situation is substituent group S1 described in the organic functions chemical combination object OSM1 and the functional structure list Member in conjunction with position it is different from the position of substituent group S2 described in the organic functions chemical combination object OSM2.

In another embodiment, feasible situation is the substituent group S1 and organic function of organic functions chemical combination object OSM1 The substituent group S2 of energy compound OSM2 is mutual constitutional isomer.

Substituent group S1 and S2 can be selected as needed, but be preferably selected from solubilizing group, crosslinkable groups and/or functional group, Such as cavity transmission group, electron transporting groups, material of main part group or broad-band gap group.Will be described in further detail later and because This is related to these groups.

In a kind of preferred configuration, mixture of the invention may include at least one organic functions chemical combination object OSM1 and extremely A kind of few organic functions chemical combination object OSM2, respectively meets logical formula (I):

(A)_q(B)_r

Formula (I)

Symbol used in it is as follows:

A is the first functional architecture unit；

B is the second structural unit, and

Q be in 1 to 20, preferably 1 to 10, particularly preferred 1 to 5 range and the integer of particularly preferably 1,2 or 3, and And

R be in 0 to 20, preferably 1 to 10, particularly preferred 1 to 5 range and the integer of particularly preferably 1,2 or 3,

Wherein the summation of q and r is at least 2, and if q or r is two or more, A or B are respectively identical or different,

Two of them constitutional isomer OSM1 and OSM2 the difference is that, at least one structural unit is in different location It is incorporated into another structural unit.

The summation of q and r be at least 2 and preferably 2 to 20, preferably 2 to 10, it is particularly preferred 2 to 5 in the range of, and Particularly preferably 2,3 or 4.

In a kind of preferred configuration, mixture of the invention can containing at least one organic functions chemical combination object OSM1 and extremely A kind of few organic functions chemical combination object OSM2, respectively contains the structure of at least one formula (II), preferably conforms to the formula:

X is identical or different in each case and is N or CR¹, preferably CR¹, or if A or B group and the atom Bonding, then X be C, condition be in a ring be no more than two X groups be N；

W is O, S, NR¹、NA、NB、C(R¹)₂、CR¹A、C(A)₂、CR¹B、C(B)₂、CAB、-R¹C=CR¹-、-R¹C=CA- ,- AC=CA- ,-R¹C=CB- ,-BC=CB- ,-BC=CA-, SO, SO₂、SiR¹ ₂Or C=O；

M is independently 0,1,2,3 or 4 in each case, preferably 0,1 or 2, and condition is label m in each ring Summation is not more than 4, preferably no greater than 2；

A is the first functional architecture unit, preferably in each case be with 5 to 40 annular atoms and can by one or Multiple R¹The aromatics or heteroaromatic ring system that substituent group replaces；

B is the second structural unit, is preferably with 5 to 40 annular atoms and can be one or more in each case R¹The aromatics or heteroaromatic ring system that substituent group replaces；

R¹It is identical or different in each case and be H, D, F, Cl, Br, I, CN, NO₂, N (Ar¹)₂, N (R²)₂, C (= O)Ar¹, C (=O) R², P (=O) (Ar¹)₂, P (Ar¹)₂, B (Ar¹)₂, B (OR²)₂, Si (Ar¹)₃, Si (R²)₃, there is 1 to 40 carbon Alkyl, alkoxy or the thio alkoxy group of the straight chain of atom, or branch or cricoid alkane with 3 to 40 carbon atoms Base, alkoxy or thio alkoxy group, or the alkenyl group with 2 to 40 carbon atoms, each of described group can quilts One or more R²Group replaces, wherein one or more non-adjacent CH₂Group can be by-R²C=CR²-、-C≡C-、Si (R²)₂、Ge(R²)₂、Sn(R²)₂, C=O, C=S, C=Se, C=NR²,-C (=O) O- ,-C (=O) NR²-、NR², P (=O) (R²) ,-O- ,-S-, SO or SO₂Instead of and wherein one or more hydrogen atoms can be by D, F, Cl, Br, I, CN or NO₂Instead of, or And it in each case can be by one or more R with 5 to 40 aromatic ring atoms²The aromatics or heteroaromatic rings that group replaces System, or there are 5 to 40 aromatic ring atoms and can be by one or more R²The aryloxy group or heteroaryloxy group that group replaces, Or there are 5 to 40 aromatic ring atoms and can be by one or more R²The aralkyl or heteroaralkyl group that group replaces, or The combination of these systems；Meanwhile two or more preferably adjacent R¹Group can form monocycle or polycyclic aliphatic, miscellaneous together Aliphatic series, aromatics or heteroaromatic ring system；

Ar¹It is identical or different in each case and be with 5 to 30 aromatic ring atoms and can be by one or more A non-aromatic R²The aromatics or heteroaromatic ring system that group replaces；Meanwhile being bonded to same silicon atom, nitrogen-atoms, phosphorus atoms or boron Two Ar of atom¹Group can also be via singly-bound bridging group or selected from B (R²)、C(R²)₂、Si(R²)₂, C=O, C=NR², C=C (R²)₂, O, S, S=O, SO₂、N(R²)、P(R²) and P (=O) R²Bridging group link together；

R²It is identical or different in each case and be H, D, F, Cl, Br, I, CN, B (OR³)₂, NO₂, C (=O) R³, CR³ =C (R³)₂, C (=O) OR³, C (=O) N (R³)₂, Si (R³)₃, P (R³)₂, B (R³)₂, N (R³)₂, NO₂, P (=O) (R³)₂, OSO₂R³, OR³, S (=O) R³, S (=O)₂R³, alkyl, alkoxy or the thio alkoxy of the straight chain with 1 to 40 carbon atom Group, or branch or cricoid alkyl, alkoxy or thio alkoxy group with 3 to 40 carbon atoms, in the group Each of can be by one or more R³Group replaces, wherein one or more non-adjacent CH₂Group can be by-R³C=CR³-、-C ≡C-、Si(R³)₂、Ge(R³)₂、Sn(R³)₂, C=O, C=S, C=NR³,-C (=O) O- ,-C (=O) NR³-、NR³, P (=O) (R³) ,-O- ,-S-, SO or SO₂Instead of and wherein one or more hydrogen atoms can be by D, F, Cl, Br, I, CN or NO₂Instead of, or And it in each case can be by one or more R with 5 to 40 aromatic ring atoms³The aromatics or heteroaromatic rings that group replaces System, or there are 5 to 40 aromatic ring atoms and can be by one or more R³The aryloxy group or heteroaryloxy group that group replaces, Or the combination of these systems；Meanwhile two or more preferably adjacent R²Substituent group can also form monocycle or polycyclic together Aliphatic series, heterolipid race, aromatics or heteroaromatic ring system；

R³It is identical or different in each case and be selected from H, D, F, CN, with 1 to 20 carbon atom aliphatic hydrocarbyl Group, or aromatics or heteroaromatic ring system with 5 to 30 aromatic ring atoms, wherein one or more hydrogen atoms can by D, F, Cl, Br, I or CN are replaced and it can be replaced by one or more respectively alkyl with 1 to 4 carbon atoms groups；Meanwhile two A or more preferably adjacent R³Substituent group can also form monocycle or polycyclic aliphatic series, heterolipid race, aromatics or heteroaromatic together Ring system；

Its condition is that the structure of the formula (II) includes at least one A and/or B group.Preferably, the knot of the formula (II) Structure includes at least one A group.

The summation of the A and/or B group is preferably 2 to 10, and particularly preferred 2 to 5, and particularly preferred 2,3 or 4 It is a.

Adjacent carbon atom in the context of the present invention is the carbon atom being bonded directly with one another.In addition, in group definition " adjacent group " refers to that these groups are bonded with same carbon atom or with adjacent carbon atom.These definition especially correspondingly apply to Term " adjacent group " and " adjacent substituents ".

In the context of the present specification, the word that two or more groups can form ring together refers in particular to, described Two groups are connected to each other by chemical bond and eliminate two hydrogen atoms in form.This is illustrated by following scheme:

However, in addition, above-mentioned word also refers to, if two groups first is that hydrogen, second group are bound to hydrogen original The bonding position of son, thus cyclic.This will be illustrated by following scheme:

Fused-aryl group in the context of the present invention, fused aromatic ring system or to condense heteroaromatic ring system be following base Group, two of them or more aromatic group (i.e. increasing ring) is fused to each other along common edge so that such as two carbon atoms belong to Few two aromatics or heteroaromatic rings, as the situation in such as naphthalene.On the contrary, for example, due to two aromatic groups in fluorenes Without common edge, therefore fluorenes is not the fused-aryl group in the context of the invention.Corresponding definition is suitable for heteroaryl base Group and can with but without contain heteroatomic condensed ring system.

Aryl group in the context of the present invention contains 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms；In this hair Heteroaryl groups in bright context contain 2 to 60 carbon atoms, preferably 2 to 40 carbon atoms and at least one hetero atom, Condition is carbon atom and heteroatomic summation is at least 5.The hetero atom is preferably selected from N, O and/or S.Aryl group or heteroaryl Base group is referred to herein as simple aromatic ring, i.e. benzene or simple heteroaromatic rings, such as pyridine, pyrimidine, thiophene etc. or thick Aryl or heteroaryl group of conjunction, such as naphthalene, anthracene, phenanthrene, quinoline, isoquinolin etc..

Aromatics ring system in the context of the present invention contains 6 to 60 carbon atoms, preferably 6 to 40 carbon originals in ring system Son.Heteroaromatic rings in the context of the present invention tie up in ring system containing 1 to 60 carbon atom, preferably 1 to 40 carbon atom and At least one hetero atom, condition is carbon atom and heteroatomic summation is at least 5.The hetero atom be preferably selected from N, O and/or S.Aromatics or heteroaromatic ring system in the context of the present invention refers to following system, need not only contain aryl or heteroaryl base Group, but plurality of aryl or heteroaryl group can also be interrupted by non-aromatic unit (10% of preferably smaller than non-H atom), The non-aromatic unit is, for example, carbon, nitrogen or oxygen atom or carbonyl group.For example, two fluorenes of such as 9,9'- spiral shell, 9,9- diaryl fluorene, Therefore the system of triarylamine, diaryl ether, Stilbene etc. should also be considered as aromatics ring system in the context of the present invention, and wherein Two or more aryl groups are also by such as straight chain or cricoid alkyl group or by the intermittent system of silyl-group So.In addition, the system that is bonded directly with one another of two of them or more aryl or heteroaryl group for example biphenyl, terphenyl, Quaterphenyl or bipyridyl should equally be considered as aromatics or heteroaromatic ring system.

Cricoid alkyl, alkoxy or thio alkoxy group in the context of the present invention refers to monocycle, bicyclic or more Cyclic group.

In the context of the present invention, wherein individual hydrogen atoms or CH₂The C that group can also be replaced by above-mentioned group₁To C₂₀ Alkyl group refers to such as methyl, ethyl, n-propyl, isopropyl, cyclopropyl, normal-butyl, isobutyl group, sec-butyl, tert-butyl, ring Butyl, 2- methyl butyl, n-pentyl, sec-amyl, tertiary pentyl, 2- amyl, neopentyl, cyclopenta, n-hexyl, Sec-Hexyl, uncle oneself Base, 2- hexyl, 3- hexyl, new hexyl, cyclohexyl, 1- methylcyclopentyl, 2- methyl amyl, n-heptyl, 2- heptyl, 3- heptyl, Bicyclic [2.2.2] octyl of 4- heptyl, suberyl, 1- methylcyclohexyl, n-octyl, 2- ethylhexyl, cyclooctyl, 1-, 2- are bicyclic [2.2.2] octyl, 2- (2,6- dimethyl) octyl, 3- (3,7- dimethyl) octyl, adamantyl, trifluoromethyl, pentafluoroethyl group, The positive hex- 1- base of 2,2,2- trifluoroethyl, 1,1- dimethyl-, the positive hept- 1- base of 1,1- dimethyl-, the positive octyl- 1- of 1,1- dimethyl- The positive decyl- 1- base of base, 1,1- dimethyl -, 1,1- dimethyl-n-dodecane -1- base, 1,1- dimethyl-n-tetradecane -1- base, 1, The positive hex- 1- base of 1- dimethyl-hexadecane -1- base, 1,1- dimethyl-n-octadecane -1- base, 1,1- diethyl -, 1,1- diethyl The positive hept- 1- base of base -, the positive octyl- 1- base of 1,1- diethyl -, the positive decyl- 1- base of 1,1- diethyl -, 1,1- diethyl-n-dodecane -1- Base, 1,1- diethyl-n-tetradecane -1- base, 1,1- diethyl-hexadecane -1- base, 1,1- diethyl-n-octadecane -1- Base, 1- (n-propyl) hexamethylene -1- base, 1- (normal-butyl) hexamethylene -1- base, 1- (n-hexyl) hexamethylene -1- base, 1- (n-octyl) ring Hex- 1- base and 1- (positive decyl) hexamethylene -1- base group.Alkenyl group refer to for example vinyl, acrylic, cyclobutenyl, pentenyl, Cyclopentenyl, hexenyl, cyclohexenyl group, heptenyl, cycloheptenyl, octenyl, cyclo-octene base or cyclo-octadiene base.Alkynyl group Refer to such as acetenyl, propinyl, butynyl, pentynyl, hexin base, heptynyl or octynyl.C₁To C₄₀Alkoxy base is Refer to for example methoxyl group, trifluoromethoxy, ethyoxyl, positive propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, Tert-butoxy or 2- methyl butoxy.

With 5-60 aromatic ring atom, preferably 5-40 aromatic ring atom and in each case can also be above-mentioned Group replaces and can be via the aromatics or heteroaromatic ring system that any desirable position is connect with aromatics or heteroaromatic system Refer to group for example derived from following substance: benzene, naphthalene, anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene, lettuce, fluoranthene, benzofluoranthrene, Aphthacene, pentacene, BaP, biphenyl, phenylbenzene fork, terphenyl, terphenyl fork, fluorenes, two fluorenes of spiral shell, dihydro phenanthrene, dihydropyrene, four It is hydrogen pyrene, cis or trans indenofluorene, cis or trans list benzo indenofluorene, cis or trans dibenzo indenofluorene, three polyindenes, different Three polyindenes, three polyindene of spiral shell, different three polyindene of spiral shell, furans, benzofuran, isobenzofuran, dibenzofurans, thiophene, benzothiophene, It is isothiophene, dibenzothiophenes, pyrroles, indoles, iso-indoles, carbazole, indolocarbazole, indeno carbazole, pyridine, quinoline, different Quinoline, acridine, phenanthridines, benzo -5,6- quinoline, benzo -6,7- quinoline, benzo -7,8- quinoline, phenthazine, phenoPiperazine, pyrazoles, Indazole, imidazoles, benzimidazole, naphtho- imidazoles, phenanthro- imidazoles, pyridine-imidazole, pyrazine and imidazoles, quinoxaline and imidazoles,Azoles, BenzoAzoles, naphtho-Azoles, anthraAzoles, phenanthro-It is azoles, differentAzoles, 1,2- thiazole, 1,3- thiazole, benzothiazole, pyridazine, benzene And pyridazine, pyrimidine, benzo pyrimidine, quinoxaline, 1,5- naphthodiazine, 2,7- diaza pyrene, 2,3- diaza pyrene, 1,6- diaza Pyrene, 1,8- diaza pyrene, 4,5- diaza pyrene, tetra- azepine of 4,5,9,10-, pyrazine, azophenlyene, phenoIt is piperazine, phenthazine, glimmering red Ring, naphthyridines, azepine carbazole, benzo carboline, phenanthroline, 1,2,3- triazole, 1,2,4- triazole, benzotriazole, 1,2,3-Diazole, 1,2,4-Diazole, 1,2,5-Diazole, 1,3,4-Diazole, 1,2,3- thiadiazoles, 1,2,4- thiadiazoles, 1,2,5- thiadiazoles, 1,3,4- thiadiazoles, 1,3,5- triazine, 1,2,4- triazine, 1,2,3- triazine, tetrazolium, 1,2,4,5- tetrazine, 1,2,3,4- tetrazine, 1,2,3,5- tetrazine, purine, pteridine, indolizine and diazosulfide.

In a kind of preferred configuration, available compound OSM1 and OSM2 can be by formula (I) and/or (II) according to the present invention Representation.Preferably, available according to the present invention the compound OSM1 and OSM2 of the structure comprising formula (I) and/or (II) Molecular weight be not more than 5000g/mol, preferably no greater than 4000g/mol, especially preferably no more than 3000g/mol, particularly preferably No more than 2000g/mol and most preferably no greater than 1200g/mol.

Furthermore feasible situation is, substituent group S1 and substituent group S2 in the compound of the present invention OSM1 and OSM2 or at least A kind of structural unit A and/or B is selected from phenyl in each case, ortho position, meta or para position xenyl, terphenyl, especially Branch terphenyl, tetrad phenyl, especially branch tetrad phenyl, 1-, 2-, 3- or 4- fluorenyl, 9,9'- diaryl fluorenyls, 1-, Two fluorenyl of 2-, 3- or 4- spiral shell, pyridyl group, pyrimidine radicals, 1-, 2-, 3- or 4- dibenzofuran group, 1-, 2-, 3- or 4- dibenzo thiophene Pheno base, pyrenyl, triazine radical, imidazole radicals, benzimidazolyl, benzoOxazolyl, benzothiazolyl, 1-, 2-, 3- or 4- carbazyl, 1- or 2- naphthalene, anthryl, preferably 9- anthryl, trans- and cis- indeno fluorenyl, indeno carbazyl, indolocarbazole base, spiral shell carbazole Base, 5- aryl-phenanthridines -6- ketone-base, 9,10- dehydrogenation phenanthryl, fluoranthene base, tolyl, mesitylene base, phenoxytoluene base, benzene Methyl ether base, triaryl amino is bis- (triaryl amino), three (triaryl amino), hexamethyl indanyl, tetralyl, mononaphthene Base, bicyclic alkyl, tricyclic alkyl, alkyl such as tert-butyl, methyl, propyl, alkoxy, alkyl sulfenyl, alkylaryl, triaryl Silicyl, trialkylsilkl, xanthyl, 10- aryl phenoPiperazine base, phenanthryl and/or terphenyl pitch base, in the group Each of can be replaced by one or more groups, but preferably unsubstituted, particularly preferred phenyl, two fluorenes of spiral shell, fluorenes, dibenzo furan It mutters, dibenzothiophenes, anthracene, phenanthrene, terphenyl fork group.In this case, above-mentioned group can be by R as described above¹Group takes Generation.

Furthermore feasible situation is that available compound OSM1 and OSM2 respectively has functional structure list according to the present invention Member, the first functional architecture unit A preferably at least one aromatics or heteroaromatic ring system, the ring system have 5 to 40 Annular atom and can be by one or more substituent groups, preferably one or more S1, S2 or R¹Substituent group replaces.

Preferably, available compound OSM1 and OSM2 can respectively contain functional architecture unit, preferably according to the present invention First functional architecture unit A selected from the following: fluorenes, indenofluorene, two fluorenes of spiral shell, carbazole, indeno carbazole, indolocarbazole, spiral shell carbazole, Pyrimidine, triazine, lactams, triarylamine, dibenzofurans, dibenzothiophenes, imidazoles, benzimidazole, benzoAzoles, benzo thiophene Azoles, 5- aryl phenanthridines -6- ketone, 9,10- dehydrogenations are luxuriant and rich with fragrance, fluoranthene, wherein the functional architecture unit can by one or more substituent groups, It is preferred that one or more S1, S2 or R¹Substituent group replaces.

Preferably, organic functions chemical combination the object OSM1 and OSM2 can respectively contain at least two functional groups, wherein described Organic functions chemical combination object OSM1 and OSM2 the difference is that described two functional groups in each case different location that This connection.Preferably, the second structural unit can have at least one aromatics or heteroaromatic ring system, and each of described ring system has It 5 to 40 annular atoms and can be substituted by one or more substituents, preferred substituent group is selected from the R above and being described later on¹ Group.Preferably, substituent group S1 and S2 can be selected from the R above and being described later on¹Group.

It is preferred that feasible situation is, the functional architecture unit of available compound OSM1 and OSM2 according to the present invention, preferably First functional architecture unit A is selected from cavity transmission group, electron transporting groups, material of main part group and broad-band gap group.

In another embodiment, available compound OSM1 and OSM2 is passed comprising at least one hole according to the present invention Defeated group, these groups are known in the art and in many cases selected from arylamino groups, preferably ammonia diaryl base Or triaryl amino group, heteroaryl amino group, preferably two heteroaryl aminos or three heteroaryl amino groups, carbazole group, Preferably carbazole group.

It is preferred that feasible situation is, cavity transmission group, structural unit A or substituent group S1 or S2 include to be selected from formula (H-1) To (H-3) group and be preferably selected from the group of formula (H-1) to (H-3)

Wherein dotted line key label link position, and

Ar²、Ar³、Ar⁴It is aryl group with 6 to 40 carbon atoms each independently or there are 3 to 40 carbon atoms Heteroaryl groups, each of described group can be by one or more R¹Group replaces；

P is 0 or 1, and

Z is CR¹ ₂、SiR¹ ₂, C=O, N-Ar¹、BR¹、PR¹、POR¹、SO、SO₂, Se, O or S, preferably CR¹ ₂、N-Ar¹, O or S, wherein the R¹Group has definition given above and Ar¹It is that there are 5 to 60 aromatic ring atoms, preferably 5 to 40 virtues Race's annular atom and can be by one or more R¹Group replace aromatics or heteroaromatic ring system, have 5 to 60 aromatic ring atoms, It is preferred that 5 to 40 aromatic ring atoms and in each case can be by one or more R¹The aryloxy group that group replaces, or With 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms and in each case can be by one or more R¹Base The aromatic alkyl group that group replaces, the preferably adjacent R of two of them or more¹Substituent group can optionally form monocycle or polycyclic rouge Race, heterolipid race, aromatics or heteroaromatic ring system, the ring system can be by one or more R²Group replaces.

Furthermore feasible situation is that cavity transmission group, structural unit A or substituent group S1, S2 include to be selected from formula (H-4) extremely (H-26) group and the group for being preferably selected from formula (H-4) to (H-26)

Wherein Y¹It is O, S, C (R¹)₂Or NAr¹, dotted line key label link position, e is 0,1 or 2, and j is 0,1,2 or 3, and h is 0,1,2,3 or 4, p are 0,1,2,3,4,5 or 6, preferably 0,1,2 or 3 and more preferably 0,1 or 2, Ar¹And Ar²With above The definition provided, especially for the definition that formula (H-1) or (H-2) provide, and R¹With definition given above, especially The definition provided for formula (II).

In group (H-1) into (H-26), preferably carbazole group, especially group (H-4) to (H-26).

In another preferred embodiment of the invention, Ar²It is that there is 5 to 14 aromatics or heteroaromatic rings atom Aromatics or heteroaromatic ring system preferably have 6 to 12 carbon atoms and can be by one or more R¹Group replace but preferably not Substituted aromatics ring system, wherein R¹There can be definition given above, the definition provided especially for formula (II).More preferably Ground, Ar²It is the aromatics ring system with 6 to 10 aromatic ring atoms or the heteroaromatic ring system with 6 to 13 heteroaromatic rings atoms, Each of described ring system can be by one or more R¹Group replaces, but preferably unsubstituted, wherein R¹Can have given above Definition, the definition provided especially for formula (II).

It is further preferred that symbol Ar shown in formula (H-1) to (H-26)²Especially there are 5 to 24 annular atoms, excellent The aryl or heteroaryl group of 6 to 13 annular atoms, more preferable 6 to 10 annular atoms is selected, so that aromatics or heteroaromatic ring system Aromatics or heteroaromatic group directly, i.e., via aromatics or the atom of heteroaromatic group, atomistic binding corresponding to other groups.

Furthermore feasible situation is, for being used as the compound OSM1 or OSM2 of hole mobile material or material of main part, formula Ar shown in (H-1) to (H-26)²Group includes with the aromatic ring no more than two condensed aromatics and/or heteroaromatic rings System does not preferably include any condensed aromatics or heteroaromatic ring system.Therefore, naphthalene structure is better than anthracene structure.In addition, fluorenyl, spiral shell Two fluorenyls, dibenzofuran group and/or dibenzothiophenes based structures are better than naphthalene structure.Do not have condensed knot particularly preferably Structure, such as phenyl, xenyl, terphenyl and/or tetrad phenyl structure.

Compound OSM1 or OSM2 as fluorescent illuminant also may include the ring system that more height is condensed, such as luxuriant and rich with fragrance, anthracene Or pyrenyl group.

Suitable aromatics or heteroaromatic ring system Ar²Example be selected from ortho position, meta or para position benzene subunit, ortho position, meta position or Para-biphenyl subunit, terphenyl subunit, especially branch terphenyl subunit, quaterphenyl subunit, especially branch quaterphenyl subunit, Fluorenes subunit, two fluorenes subunit of spiral shell, dibenzofurans subunit, dibenzothiophenes subunit and carbazole subunit, each of described group can By one or more R¹Group replaces, but preferably unsubstituted.

Furthermore feasible situation is Ar shown in formula (H-1) to (H-26)²Group especially has no more than 1 nitrogen original Son, preferably more than 2 hetero atoms are particularly preferably no more than 1 hetero atom and particularly preferably without hetero atom.

In another preferred embodiment of the invention, Ar³And/or Ar⁴It is identical or different in each case, and It and is with 6 to 24 aromatic ring atoms, the aromatics of preferably 6 to 18 aromatic ring atoms or heteroaromatic ring system, and more preferably It is the aromatics ring system with 6 to 12 aromatic ring atoms or the heteroaromatic ring system with 6 to 13 aromatic ring atoms, the ring system Each of can be by one or more R¹Group replaces, but preferably unsubstituted, wherein R¹There can be definition given above, especially It is the definition provided in formula (II).Suitable Ar³And/or Ar⁴The example of group is selected from phenyl, ortho position, meta or para position connection Phenyl, terphenyl, especially branch terphenyl, tetrad phenyl, especially branch tetrad phenyl, 1-, 2-, 3- or 4- fluorenes Base, two fluorenyl of 1-, 2-, 3- or 4- spiral shell, pyridyl group, pyrimidine radicals, 1-, 2-, 3- or 4- dibenzofuran group, 1-, 2-, 3- or 4- bis- Benzothienyl and 1-, 2-, 3- or 4- carbazyl, each of described group can be by one or more R³Group replaces, but excellent It selects unsubstituted.

Preferably, the R¹The group not R with formula (H-1) into (H-26)¹Group bonding aryl group or heteroaryl Group Ar¹、Ar²、Ar³And/or Ar⁴Annular atom form condensed ring system.This includes and feasible R²、R³Substituent group forms fused rings System, the R²、R³Substituent group can be with R¹Group bonding.

In one preferred embodiment, available compound OSM1 and OSM2, preferably the first function according to the present invention Structural unit A can include electron transporting groups in each case, wherein the functional architecture unit or substituent group S1 and S2 can Preferably comprise electron transporting groups.Electron transporting groups be it is widely known in technical field and promote compound transport and/ Or the ability of conduction electronics.

Furthermore it is preferred that the structure comprising at least one formula (I) and/or (II) or its preferred embodiment is according to the present invention Available compound OSM1 and OSM2 presents astonishing advantage, wherein formula (I) and/or (II) or its preferred embodiment In A and/or B group or substituent group S1 and S2 include at least one structure selected from the following: pyridine, pyrazine, is rattled away at pyrimidine Piperazine, triazine, quinazoline, quinoxaline, quinoline, isoquinolin, imidazoles and/or benzimidazole, particularly preferred pyrimidine, triazine and quinoline azoles Quinoline.

In the preferred configuration of one kind of the invention, feasible situation is electron transporting groups, structural unit A and/or B, Substituent group S1, S2 or a R¹Group includes can be by the group of formula (QL) expression, the group that can be preferably indicated by formula (QL),

Q——L¹-----

Formula (QL)

Wherein L¹It represents key or there are 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms and can be by one Or multiple R¹The aromatics or heteroaromatic ring system that group replaces, and Q is electron transporting groups, wherein R¹With given above fixed Justice, the definition provided especially for formula (II).

Furthermore feasible situation is electron transporting groups, especially Q group and/or substituent group S1 shown in formula (QL) or S2 is selected from the knot of formula (Q-1), (Q-2), (Q-3), (Q-4), (Q-5), (Q-6), (Q-7), (Q-8), (Q-9) and/or (Q-10) Structure,

Wherein dotted line key label link position,

Q' is identical or different in each case and is CR¹Or N, and

Q " is NR¹, O or S；

Wherein at least one Q' is N, and

R¹Such as above for defined in formula (II).

Preferably, Q group shown in electron transporting groups, especially formula (QL) and/or substituent group S1 or S2 can be selected from formula (Q-11), the structure of (Q-12), (Q-13), (Q-14) and/or (Q15)

Wherein symbol R¹With the definition provided especially with respect to formula (II), X is N or CR¹And dotted line key label connection position It sets, wherein X is preferably nitrogen-atoms.

In another embodiment, Q group shown in electron transporting groups, especially formula (QL) and/or substituent group S1 Or S2 can be selected from formula (Q-16), the structure of (Q-17), (Q-18), (Q-19), (Q-20), (Q-21) and/or (Q22),

Wherein symbol R¹With above especially with respect to definition described in formula (II), dotted line key label link position and m is 0,1,2,3 or 4, preferably 0,1 or 2, n are 0,1,2 or 3, preferably 0,1 or 2, and o is 0,1 or 2, preferably 1 or 2.This Place is preferably the structure of formula (Q-16), (Q-17), (Q-18) and (Q-19).

In another embodiment, Q group shown in electron transporting groups, especially formula (QL) and/or substituent group S1 Or S2 can be selected from formula (Q-23), the structure of (Q-24) and/or (Q-25),

Wherein symbol R¹With above especially with respect to definition described in formula (II), and dotted line key label link position.

In another embodiment, Q group shown in electron transporting groups, especially formula (QL) and/or substituent group S1 Or S2 can be selected from formula (Q-26), the structure of (Q-27), (Q-28), (Q-29) and/or (Q-30),

Wherein X is N or CR¹, symbol R¹With the definition provided above especially with respect to formula (II), dotted line key label connection position It sets, wherein X is preferably nitrogen-atoms, and Ar¹Be with 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms and It in each case can be by one or more R¹Group replace aromatics or heteroaromatic ring system, have 5 to 60 aromatic ring atoms, It is preferred that 5 to 40 aromatic ring atoms and can be by one or more R¹The aryloxy group that group replaces, or there are 5 to 60 virtues Race's annular atom, preferably 5 to 40 aromatic ring atoms and in each case can be by one or more R¹The aralkyl that group replaces Base group, the preferably adjacent R of two of them or more¹Substituent group can optionally form monocycle or polycyclic aliphatic series, heterolipid race, virtue Race or heteroaromatic ring system, preferably monocycle or polycyclic aliphatic ring systems, the ring system can be by one or more R²Group replaces.

Preferably, Q group shown in electron transporting groups, especially formula (QL) and/or substituent group S1 or S2 can be selected from formula (Q-31)、(Q-32)、(Q-33)、(Q-34)、(Q-35)、(Q-36)、(Q-37)、(Q-38)、(Q-39)、(Q-40)、(Q-41)、 (Q-42), the structure of (Q-43) and/or (Q-44),

Wherein symbol Ar¹With above especially with respect to definition described in formula (Q-26), (Q-27) or (Q-28), and R¹Tool Have above especially with respect to definition described in formula (II), dotted line key label link position and m is 0,1,2,3 or 4, preferably 0,1 Or 2, n is 0,1,2 or 3, preferably 0,1 or 2, and l is 1,2,3,4 or 5, preferably 0,1 or 2.

Preferably, symbol Ar¹It is aryl or heteroaryl group, so that the aromatics or heteroaromatic base of aromatics or heteroaromatic ring system It rolls into a ball directly, i.e., via aromatics or the atom of heteroaromatic group, atom corresponding to other groups, such as (H- illustrated above 1) to (H-26) or (Q-26) to the carbon or nitrogen atom bonding of (Q-44) group.

In another preferred embodiment of the invention, Ar¹It is identical or different in each case and be have 6 To 24 aromatic ring atoms, the aromatics of preferably 6 to 18 aromatic ring atoms or heteroaromatic ring system, and more preferably have 6 to The aromatics ring system of 12 aromatic ring atoms or heteroaromatic ring system with 6 to 13 aromatic ring atoms, each of described ring system It can be by one or more R¹Group replaces, but preferably unsubstituted, wherein R¹There can be definition given above, especially in formula (II) definition provided in.Suitable Ar¹The example of group be selected from phenyl, ortho position, meta or para position xenyl, terphenyl, Especially branch terphenyl, tetrad phenyl, especially branch tetrad phenyl, 1-, 2-, 3- or 4- fluorenyl, 1-, 2-, 3- or 4- Two fluorenyl of spiral shell, pyridyl group, pyrimidine radicals, 1-, 2-, 3- or 4- dibenzofuran group, 1-, 2-, 3- or 4- dibenzothiophene and 1-, 2-, 3- or 4- carbazyl, each of described group can be by one or more R³Group replaces, but preferably unsubstituted.

Advantageously, Ar of the formula (H-1) to (H-26) or (Q-16) into (Q-34)¹It is that there are 6 to 12 aromatic ring originals Son and can be by one or more R¹Group replaces but preferred unsubstituted aromatics ring system, wherein R¹There can be above-mentioned definition, especially It is for definition described in formula (I).

Furthermore feasible situation is Ar¹、Ar²、Ar³And/or Ar⁴Group is selected from phenyl, ortho position, meta or para position biphenyl Base, terphenyl, especially branch terphenyl, tetrad phenyl, especially branch tetrad phenyl, 1-, 2-, 3- or 4- fluorenyl, Two fluorenyl of 1-, 2-, 3- or 4- spiral shell, pyridyl group, pyrimidine radicals, 1-, 2-, 3- or 4- dibenzofuran group, 1-, 2-, 3- or 4- hexichol Bithiophene base, pyrenyl, triazine radical, imidazole radicals, benzimidazolyl, benzoOxazolyl, benzothiazolyl, 1-, 2-, 3- or 4- carbazole Base, 1- or 2- naphthalene, anthryl, preferably 9- anthryl, phenanthryl and/or terphenyl pitch base, each of described group can by one or Multiple R¹Group replaces, but preferably unsubstituted, particularly preferably phenyl, two fluorenes of spiral shell, fluorenes, dibenzofurans, dibenzo thiophene Pheno, anthracene, phenanthrene, terphenyl pitch group, wherein the R¹Group has definition given above, provides especially for formula (II) Definition.

Preferably, R of the formula (H-1) to (H-26) or (Q-1) into (Q-44)¹Group not with R¹The heteroaryl that group is bonded Base group or Ar¹And/or Ar²The annular atom of group forms condensed ring system.This includes and feasible R²、R³Substituent group forms condensed Ring system, the R²、R³Substituent group can be with R¹Group bonding.

Furthermore feasible situation is R¹Substituent group not with R¹The annular atom of aromatics or heteroaromatic ring system that substituent group is combined Form condensed aromatics or heteroaromatic ring system, preferably any condensed ring system.This includes and feasible R²、R³Substituent group forms condensed Ring system, the R²、R³Substituent group can be with R¹Group bonding.It is preferred that feasible situation is, the R of aromatics or heteroaromatic ring system¹Substituent group Ring system is not formed with aromatics or the annular atom of heteroaromatic ring system.This includes and feasible R²、R³Substituent group forms ring system, the R²、 R³Substituent group can be with R¹Group bonding.

When X is CR¹When or when aromatics and/or heteroaromatic group are by R¹When substituent group replaces, these R¹Substituent group preferably selects From H, D, F, CN, N (Ar¹)₂, C (=O) Ar¹, P (=O) (Ar¹)₂, the alkyl or alkoxy of the straight chain with 1 to 10 carbon atom Group, or the branch with 3 to 10 carbon atoms or cricoid alkyl or alkoxy base, or with 2 to 10 carbon atoms Alkenyl group, each of described group can be by one or more R²Group replaces, wherein one or more non-adjacent CH₂Base Group can be replaced by O and wherein one or more hydrogen atoms can be replaced by D or F, have 5 to 24 aromatic ring atoms and every It can be by one or more R in the case of kind²Group substitution but preferably unsubstituted aromatics or heteroaromatic ring system, or have 5 to 25 A aromatic ring atom and can be by one or more R²The aralkyl or heteroaralkyl group that group replaces；Meanwhile it being bonded to same Two R of one carbon atom or adjacent carbon atom¹Substituent group can optionally form monocycle or polycyclic aliphatic series, aromatics or heteroaromatic rings System, the ring system can be by one or more R¹Group replaces, wherein Ar¹It is identical or different in each case and be have 5 to 40 aromatic ring atoms and in each case can be by one or more R²The aromatics or heteroaromatic ring system that group replaces, have 5 to 40 aromatic ring atoms and can be by one or more R²The aryloxy group that group replaces, or there are 5 to 40 aromatic rings Atom and in each case can be by one or more R²The aromatic alkyl group that group replaces, two of them or more are preferred Adjacent R²Substituent group can optionally form monocycle or polycyclic aliphatic series, heterolipid race, aromatics or heteroaromatic ring system, preferably monocycle or more The aliphatic ring systems of ring, the ring system can be by one or more R³Group replaces, wherein the symbol R²It is given above fixed to have Justice, the definition provided especially for formula (II).Preferably, Ar¹It is identical or different in each case and be have 5 to 24 A and preferably 5 to 12 aromatic ring atoms and in each case can be by one or more R²Group replace but preferably not by Substituted aryl or heteroaryl group.

Suitable Ar¹The example of group is selected from phenyl, ortho position, meta or para position xenyl, terphenyl, especially branch Terphenyl, tetrad phenyl, especially branch tetrad phenyl, 1-, 2-, 3- or 4- fluorenyl, two fluorenyl of 1-, 2-, 3- or 4- spiral shell, pyrrole Piperidinyl, pyrimidine radicals, 1-, 2-, 3- or 4- dibenzofuran group, 1-, 2-, 3- or 4- dibenzothiophene and 1-, 2-, 3- or 4- click Oxazolyl, each of described group can be by one or more R²Group replaces, but preferably unsubstituted.

It is highly preferred that these R¹Substituent group is selected from H, D, F, CN, N (Ar¹)₂, with 1 to 8 carbon atom, preferably have 1, 2, the linear alkyl groups of 3 or 4 carbon atoms, or branch with 3 to 8 carbon atoms, preferably with 3 or 4 carbon atoms or Cricoid alkyl group, or with 2 to 8 carbon atoms, preferably with the alkenyl group of 2,3 or 4 carbon atoms, in the group Each of can be by one or more R²Group replace, but preferably it is unsubstituted, or have 6 to 24 aromatic ring atoms, preferably 6 to 18 aromatic ring atoms, more preferable 6 to 13 aromatic ring atoms and in each case can be by one or more non-aromatic R¹ Group substitution but preferably unsubstituted aromatics or heteroaromatic ring system；Meanwhile being bonded to same carbon atom or adjacent carbon atom Two R¹Substituent group can optionally form monocycle or polycyclic aliphatic ring systems, and the ring system can be by one or more R²Group replaces, but It is preferred that unsubstituted, wherein Ar¹There can be above-mentioned definition.

Most preferably, the R¹Substituent group is selected from H and has 6 to 18 aromatic ring atoms, preferably 6 to 13 aromatic ring originals Son and in each case can be by one or more non-aromatic R²Group replaces but preferred unsubstituted aromatics or heteroaromatic Ring system.Suitable R¹The example of substituent group is selected from phenyl, ortho position, meta or para position xenyl, terphenyl, especially branch three Xenyl, tetrad phenyl, especially branch tetrad phenyl, 1-, 2-, 3- or 4- fluorenyl, two fluorenyl of 1-, 2-, 3- or 4- spiral shell, pyridine Base, pyrimidine radicals, 1-, 2-, 3- or 4- dibenzofuran group, 1-, 2-, 3- or 4- dibenzothiophene and 1-, 2-, 3- or 4- carbazole Base, each of described group can be by one or more R²Group replaces, but preferably unsubstituted.

Furthermore feasible situation is that organic functions chemical combination object OSM1 and OSM2 respectively contain at least one group, preferably S1 With S2 substituent group；Preferably, in formula (I) and/or the structure of (II), at least one structural unit A and/or B or at least one Ar¹、Ar²、Ar³、Ar⁴And/or R¹Group includes to be selected from formula (R¹- 1) to (R¹- 95) group is preferably selected from formula (R¹- 1) extremely (R¹- 95) group,

Symbol used in it is as follows:

Y is O, S or NR², preferably O or S；

I is independently 0,1 or 2 in each case；

J is independently 0,1,2 or 3 in each case；

H is independently 0,1,2,3 or 4 in each case；

G is independently 0,1,2,3,4 or 5 in each case；

R²There can be definition given above, especially for the definition that formula (II) provides, and

Dotted line key label link position.

It is preferred that feasible situation is, formula (R¹- 1) to (R¹- 95) mark the summation of i, j, h and g in each case in structure It is not more than 3, preferably no greater than 2 and more preferably no more than 1 down.

Preferably, formula (R¹- 1) to (R¹- 95) R in²Group not with R²The aryl group or heteroaryl base that group is bonded The annular atom of group forms condensed aromatics or heteroaromatic ring system, and does not preferably form any condensed ring system.This include with it is feasible R³Substituent group forms condensed ring system, the R³Substituent group can be with R²Group bonding.

Furthermore feasible situation is, constitutional isomer compound OSM1 and OSM2 include at least one linking group, so that At least one functional architecture unit is bonded with other structural unit；Preferably, the linking group is that have in each case There are 5 to 40 annular atoms and can be for example by R as described above¹The aromatics or heteroaromatic ring system that group replaces.Preferably, described Other structural unit can be cavity transmission group, electron transporting groups, solubilized structural unit, crosslinkable groups or cause to lead The group of body material or the material with broad-band gap characteristic.

In addition, the constitutional isomer OSM1 and OSM2 may include at least one linking group, so that at least one is solubilized Structural unit is bonded with functional architecture unit；Preferably, the linking group is that have 5 to 40 annular atoms in each case And it can be for example by R as described above¹The aromatics or heteroaromatic ring system that group replaces.

It can be by preferred linking group that constitutional isomer OSM1 and OSM2 are covered below in association with formula illustrated above (QL) L present in¹Group citing is described in detail.Preferably, the L¹Group can be with Q group and aromatics or heteroaromatic group or formula (QL) L¹The nitrogen-atoms that group is bonded forms total conjugated.Once being formed between adjacent aromatics or heteroaromatic rings direct Key is formed the total conjugated of aromatics or heteroaromatic system.Between above-mentioned conjugation group for example via sulphur, nitrogen or oxygen atom or Other keys of carbonyl group are harmless to being conjugated.In the case where fluorenes system, two aromatic ring Direct Bondings, wherein in 9 sp³ Hydbridized carbon atoms do not prevent the condensed of these rings, but it is feasible for being conjugated, because of 9 sp³The different positioning of hydbridized carbon atoms In electron-transport Q group and it is fluorene structured between.On the contrary, in the case where the second spiral shell two is fluorene structured, if Q group and formula (QL) L¹Between the aromatics or heteroaromatic group that group is bonded be bonded in spiral shell two it is fluorene structured in be via same phenyl group or It is that can then form total conjugated via bonding directly with one another and phenyl group in one plane in spiral shell two is fluorene structured. If the L of Q group and formula (QL)¹The key between aromatics or heteroaromatic group that group is bonded is via the sp for passing through 9³It is miscellaneous Different phenyl groups during second spiral shell two of change carbon atom bonding is fluorene structured, then be conjugated interruption.

In another preferred embodiment of the invention, L¹It is key or has 5 to 14 aromatics or heteroaromatic rings former The aromatics of son or heteroaromatic ring system preferably have 6 to 12 carbon atoms and can be by one or more R¹Group replace but it is excellent Unsubstituted aromatics ring system is selected, wherein R¹There can be definition given above, the definition provided especially for formula (II).More Preferably, L¹It is the aromatics ring system with 6 to 10 aromatic ring atoms or the heteroaromatic rings with 6 to 13 heteroaromatic rings atoms System, each of described ring system can be by one or more R²Group replaces, but preferably unsubstituted, wherein R²Can have above to Definition out, the definition provided especially for formula (II).

It is further preferred that symbol L shown in formula (QL)¹It is especially identical or different in each case and be key or Aryl or heteroaryl group with 5 to 24 annular atoms, preferably 6 to 13 annular atoms, more preferable 6 to 10 annular atoms, makes Aromatics or heteroaromatic ring system aromatics or heteroaromatic group directly, i.e., via aromatics or the atom of heteroaromatic group, with it The corresponding atomistic binding of its group.

In addition feasible situation is L shown in formula (QL)¹Group include have be no more than two condensed aromatics and/ Or the aromatics ring system of heteroaromatic rings, preferably do not include any condensed aromatics or heteroaromatic ring system.Therefore, naphthalene structure is better than anthracene Structure.In addition, fluorenyl, two fluorenyl of spiral shell, dibenzofuran group and/or dibenzothiophenes based structures are better than naphthalene structure.

Do not have condensed structure, such as phenyl, xenyl, terphenyl and/or quaterphenyl base junction particularly preferably Structure.

Suitable aromatics or heteroaromatic ring system L¹Example be selected from ortho position, meta or para position benzene subunit, ortho position, meta position or right Position biphenyl subunit, terphenyl subunit, especially branch terphenyl subunit, quaterphenyl subunit, especially branch quaterphenyl subunit, fluorenes Subunit, two fluorenes subunit of spiral shell, dibenzofurans subunit, dibenzothiophenes subunit and carbazole subunit, each of described group can quilts One or more R²Group replaces, but preferably unsubstituted.

Furthermore feasible situation is L shown in formula (QL)¹Group especially has no more than 1 nitrogen-atoms, does not preferably surpass It crosses 2 hetero atoms, be particularly preferably no more than 1 hetero atom and more preferably without hetero atom.

The preferably compound OSM1 and OSM2 of the structure comprising at least one formula (H-1) to (H-26), wherein Ar²Base Group is selected from formula (L¹- 1) to (L¹- 109) group, and/or preferably comprising the compound OSM1 of at least one linking group And OSM2, and/or the compound OSM1 and OSM2 of the preferably structure comprising formula (QL), wherein L¹Group is that key either selects From formula (L¹- 1) to (L¹- 109) group,

Wherein dotted line key marks link position in each case, and label k is 0 or 1, and label l is 0,1 or 2, and label j exists It is independently 0,1,2 or 3 in each case；Marking h is independently 0,1,2,3 or 4 in each case, label g is 0,1,2, 3,4 or 5；Symbol Y is O, S or NR², preferably O or S；And symbol R²With definition given above, especially for formula (II) definition provided.

It is preferred that feasible situation is, in formula (L¹- 1) to (L¹- 109) mark the summation of k, l, g, h and j every in structure It is at most 3, preferably up to 2 and more preferably up to 1 in the case of kind.

Preferred the compounds of this invention with formula (QL) group includes L group, represents key or it is selected from formula (L¹- 1) to (L¹- 78) and/or (L¹- 92) to (L¹One of -109), preferred formula (L¹- 1) to (L¹- 54) and/or (L¹- 92) to (L¹- One of 108), particularly preferred formula (L¹- 1) to (L¹- 29) and/or (L¹- 92) to (L¹One of -103).Advantageously, in formula (L¹- 1) to (L¹- 78) and/or (L¹- 92) to (L¹- 109), preferred formula (L¹- 1) to (L¹- 54) and/or (L¹- 92) to (L¹- 109), Particularly preferred formula (L¹- 1) to (L¹- 29) and/or (L¹- 92) to (L¹- 103) in structure, the summation of label k, l, g, h and j exist It in each case can be no more than 3, preferably no greater than 2 and more preferably no more than 1.

The preferred the compounds of this invention of group with formula (H-1) to (H-26) includes Ar²Group is selected from formula (L¹- 1) to (L¹- 78) and/or (L¹- 92) to (L¹One of -109), preferred formula (L¹- 1) to (L¹- 54) and/or (L¹- 92) to (L¹- One of 108), particularly preferred formula (L¹- 1) to (L¹- 29) and/or (L¹- 92) to (L¹One of -103).Advantageously, in formula (L¹- 1) to (L¹- 78) and/or (L¹- 92) to (L¹- 109), preferred formula (L¹- 1) to (L¹- 54) and/or (L¹- 92) to (L¹- 108), Particularly preferred formula (L¹- 1) to (L¹- 29) and/or (L¹- 92) to (L¹- 103) in structure, the summation of label k, l, g, h and j exist It in each case can be no more than 3, preferably no greater than 2 and more preferably no more than 1.

Preferably, formula (L¹- 1) to (L¹- 109) R in²Group not with R²The aryl group or heteroaryl that group is bonded The annular atom of group forms condensed aromatics or heteroaromatic ring system, and does not preferably form any condensed ring system.This include with can Capable R³Substituent group forms condensed ring system, the R³Substituent group can be with R²Group bonding.

When available compound OSM1 and OSM2 according to the present invention is by aromatics or heteroaromatic R¹Or R²When group replaces, especially Be in the case where it is configured for green or the material of main part of red OLED, electron transport material or hole mobile material, Preferably they do not have any aryl or heteroaryl group with the aromatics hexatomic ring condensed directly with one another more than two. It is highly preferred that the substituent group does not have any aryl or heteroaryl group with hexatomic ring condensed directly with one another completely. The reason of this preferred feature, is the low triplet energies of this structure.With the aromatics six condensed directly with one another more than two Member ring but the fused-aryl group being still adapted to according to the present invention are luxuriant and rich with fragrance and terphenyl forks, because these also have high triplet Energy level.

It is used as fluorescent illuminant in available compound OSM1 and OSM2 according to the present invention or as Blue OLED material Under configuring condition, preferred compound can contain corresponding group, such as fluorenes, anthracene and/or pyrenyl group, can be by R²Group replace or Person its pass through (R¹- 1) to (R¹- 95) group, preferably (R¹- 33) to (R¹- 57) and (R¹- 76) to (R¹- 86) or (L¹- 1) to (L¹- 109), preferably (L¹- 30) to (R¹- 60) and (R¹- 71) to (R¹- 91) by R²The corresponding substitution of substituent group is formed.

In another preferred embodiment of the invention, such as in the preferred implementation side of formula (II) structure and the structure It formula or in which refers in the structures of these formulas, R²It is identical or different in each case and be selected from H, D, have 1 to 10 carbon Atom, preferably with the aliphatic hydrocarbyl group of 1,2,3 or 4 carbon atom, or with 5 to 30 aromatic ring atoms, preferably with 5 There can be to 24 aromatic ring atoms, more preferably with 5 to 13 aromatic ring atoms and respectively 1 to 4 by one or more The alkyl group substitution of carbon atom but preferably unsubstituted aromatics or heteroaromatic ring system.

In another preferred embodiment of the invention, such as in the preferred implementation side of formula (II) structure and the structure It formula or in which refers in the structures of these formulas, R³It is identical or different in each case and be selected from H, D, F, CN, have 1 to 10 A carbon atom preferably with the aliphatic hydrocarbyl group of 1,2,3 or 4 carbon atom, or has 5 to 30 aromatic ring atoms, preferably Can have with 5 to 24 aromatic ring atoms, more preferably with 5 to 13 aromatic ring atoms and respectively 1 by one or more Alkyl group substitution but preferred unsubstituted aromatics or heteroaromatic ring system to 4 carbon atoms.

In another arrangement, feasible situation is that compound OSM1 and OSM2 used according to the invention respectively have At least one solubilizing group.Therefore, in above-mentioned configuration, substituent group S1, substituent group S2 and/or group B may include solubilized structure Unit preferably comprises solubilized structural unit.

Particularly preferred mixture according to the present invention, wherein organic functions chemical combination object OSM1 and OSM2 respectively contains at least one A solubilizing group, wherein the organic functional close object OSM1 and OSM2 the difference is that, organic functions chemical combination object OSM1 Solubilizing group with OSM2 is mutual constitutional isomer, preferably comprises the aromatics of identical quantity or heteroaromatic ring system and has There is substantially the same substituent group.

Preferably, solubilizing group or solubilized structural unit may include preferably comprising longer alkyl group (about 4 to 20 Carbon atom), especially branched alkyl group, or the aryl group optionally replaced.Preferred aryl group includes xylyl, Trimethylphenyl, terphenyl or tetrad phenyl group, particularly preferred branch terphenyl or tetrad phenyl group.

In another arrangement, feasible situation is that compound OSM1 and OSM2 used according to the invention respectively have At least one crosslinkable groups.Therefore, in above-mentioned configuration, substituent group S1, substituent group S2 and/or group B may include cross-linking Group preferably comprises crosslinkable groups, can optionally be considered as structural unit.

As described above, available compound OSM1 and OSM2 can contain one or more crosslinkable groups according to the present invention. " crosslinkable groups " are the functional groups for referring to irreversibly react.This results in insoluble cross-linked materials.Can usually it pass through Heating promotes to be crosslinked by UV radiation, microwave radiation, x-radiation or electron beam.In this case, in crosslinking almost without By-product is formed.In addition, the crosslinkable groups that may be present in functional compounds are very easy to crosslinking, so that crosslinking needs relatively A small amount of energy (such as in the case of thermal crosslinking < 200 DEG C).

The example of crosslinkable groups is the unit containing double bond, three keys, and the precursor of double or triple bonds can be formed in situ, or The heterocyclic group of addition polymerizable.Crosslinkable groups include vinyl, alkenyl, preferred vinyl and acrylic, C_4-20Cycloalkenyl, Azide, ethylene oxide, oxetanes, two (alkyl) amino, cyanate, hydroxyl, glycidol ether, acrylic acid C_1-10Alkane Base ester, methacrylic acid C_1-10Arrcostab, alkenyloxy group, optimal ethylene oxygroup, perfluoro alkene oxygen base, preferably perfluoroethylene oxygroup, alkynes Base, preferably acetenyl, maleimide, cyclobutylphenyl, three (C_1-4) alkyl siloxy and three (C_1-4) alkylsilyl groups Base.Particularly preferred cyclobutylphenyl, vinyl and alkenyl.

Preferably, constitutional isomer organic functions chemical combination object OSM1 and OSM2 can be respectively containing at least one solubilized structure lists Member or solubilizing group and at least one functional architecture unit or functional group, the functional architecture unit or functional group pass selected from hole Defeated group, electron transporting groups lead to the structural unit or group of material of main part, or the structural unit with broad-band gap characteristic or Group.

Preferably, constitutional isomer organic functions chemical combination object OSM1 and OSM2 can respectively contain at least one cross-linking structure Unit or crosslinkable groups and at least one functional architecture unit or functional group, the functional architecture unit or functional group are selected from sky Cave transport group, electron transporting groups lead to the structural unit or group of material of main part, or the structure list with broad-band gap characteristic Member or group.

Statement " structural unit or group with broad-band gap characteristic " elaborates that compound OSM1 and OSM2 each can use by oneself Make wide bandgap material, therefore compound OSM1 and OSM2 have corresponding group.This, which is equally applicable to statement, " leads to material of main part Structural unit or group ".These statements are well known in the art, and also more detailed below in association with other materials Carefully illustrate.In this regard it is to be noted that compound OSM1 and OSM2 are constitutional isomers, their structure is different.Therefore, it answers When understanding subsequent comment, so that specifically mentioned compound and other constitutional isomer compound combination use.In addition, bright The compound really referred to can be easily varied by substitution appropriate, and the two kinds of structures used as a mixture are different Structure body compound.Substituent group can according to need selection in principle, but they are preferably selected from above-mentioned substituent group S1, S2 and/or R¹, Functional group, solubilizing group or crosslinkable groups are preferably selected as substituent group as described above.

In many cases, the properties of the interface track being described below describe organic functional material.Via Quantum chemistry calculation determines the molecular orbit of the material, especially highest occupied molecular orbital (HOMO) and minimum does not account for molecule Track (LUMO), energy level and minimum triplet T₁Energy and lowest excited singlet state S₁Energy.In order to calculate no metal Organic substance, geometry knot is carried out by " ground state/semiempirical/default spin/AM1/ charge 0/ spin singlet state " method first Structure optimization.Energy balane is realized subsequently, based on the geometry of optimization.This uses " TD-SCF/DFT/ defaults spin/B3PW91 " Method and " 6-31G (d) " basis set (charge 0, spin singlet state) carry out.For metal-containing compound, via " ground state/ Hartree-Fock/ defaults the spin/spin of LanL2MB/ charge 0/ singlet state " method geometry optimization.Similar to above-mentioned pass Energy balane is realized in the method for organic substance, difference is to use " LanL2DZ " basis set for metallic atom, and for ligand Use " 6-31G (d) " basis set.The HOMO energy level HEh or lumo energy LEh measured with Hartree units is obtained from energy balane. This is as follows by cyclic voltammetry measurement calibration with electronic voltmeter for determining HOMO and lumo energy:

HOMO (eV)=((HEh*27.212) -0.9899)/1.1206

LUMO (eV)=((LEh*27.212) -2.0041)/1.385

In the context of this application, these values are considered as the HOMO and lumo energy of the material.

Minimum triplet T₁It is defined as with the triplet energy from the obvious minimum energy of the quantum chemistry calculation Amount.

Lowest excited singlet state S₁It is defined as with the excitation from the obvious minimum energy of the quantum chemistry calculation Singlet energy.

Method described herein is unrelated with software package used and provides identical result always.It is common for this purpose The example of program is " Gaussian09W " (Koss Corp.) and Q-Chem 4.1 (Q-Chem company).

Compound or group or structural unit with hole-injection characteristics, referred to herein as hole-injecting material, Promote or realize for hole, that is, positive charge to be transferred in organic layer from anode.In general, the HOMO energy level of hole-injecting material is in sun In extremely horizontal or higher range, i.e., typically at least -5.3eV.

Compound or group or structural unit with hole transporting properties, referred to herein as hole mobile material, Can transporting holes, that is, positive charge, usually from anode or adjoining course for example hole injection layer inject.Hole mobile material is usual High HOMO energy level with preferably at least -5.4eV.According to the structure of electronic device, hole mobile material conduct also can be used Hole-injecting material.

Preferred compound or group or structural unit with hole injection and/or hole transporting properties include such as three virtues Base amine, benzidine, four aryl-p-phenylenediamine, triaryl phosphine, phenthazine, phenoPiperazine, dihydrophenazine, thianthrene, dibenzo is to dioxy Oneself miscellaneous bright-coloured ring, phenoThiophene, carbazole, azulenes, thiophene, pyrroles and furan derivatives and have high position HOMO (HOMO=highest Occupied molecular orbital) other heterocyclic compounds containing O, S or N.

It is to be noted that the compound or group or structure list below with hole injection and/or hole transporting properties Member: phenylenediamine derivative (US 3615404), arylamine derivatives (US 3567450), the chalcone derivative that amino replaces (US 3526501), styrylanthracene derivatives (JP-A-56-46234), polynuclear aromatic compound (EP 1009041) gather virtue Base alkane derivatives (US 3615402), fluorenone derivatives (JP-A-54-110837), hydazone derivative (US 3717462), acyl group Hydrazone, stilbene derivative (JP-A-61-210363), silazane derivatives (US 4950950), polysilane (JP-A-2-204996), benzene Amine copolymer object (JP-A-2-282263), thiophene oligomers (JP Heisei 1 (1989) 211399), polythiophene, poly- (N- vinyl click Azoles) (PVK), polypyrrole, polyaniline and other conductive macromoleculars, porphyrin compound (JP-A-63-2956965, US 4720432), aromatics diformazan Asia radical-type compound, carbazole compound, such as CDBP, CBP, mCP, aromatic uncle amine and styrylamine Compound (US 4127412), such as benzidine type triphenylamine, styrylamine type triphenylamine and diamine type triphenylamine.It can also make With arylamine dendritic macromole (JP Heisei 8 (1996) 193191), monomelic triarylamines (US 3180730), have one or Multiple vinyl groups and/or the triarylamine (US 3567450 and US 3658520) of at least one functional group containing reactive hydrogen Or four aryl diamine (two tertiary amine units are connected via aryl group).Even more triaryl amino also may be present in molecule Group.Equally suitable is phthalocyanine derivates, naphthalocyanine derivative, butadiene derivatives and quinoline, such as two pyrazines And [2,3-f:2', 3'-h] quinoxaline pregnancy nitrile.

Preferably with aromatic uncle amine (2008/0102311 A1, US 4720432 of US of at least two tertiary amine units With US 5061569), such as NPD (bis- [N- (1- the naphthalene)-N- phenyl amino] biphenyl of α-NPD=4,4'-) (US 5061569), TPD 232 (bis- (N, N'- diphenyl -4- the aminophenyl)-N of=N, N'-, N- diphenyl -4,4'- diaminostilbene, 1'- biphenyl) or MTDATA (MTDATA or m-MTDATA=4,4', 4 "-three [3- (aminomethyl phenyl) phenyl amino] triphenylamines) (JP-A-4- 308688), TBDB (=N, N, N', N'- tetra- (4- biphenyl) benzidine subunit), TAPC (bis- (the 4- di-p-tolyls of=1,1- Aminophenyl) hexamethylene), TAPPP (bis- (4- di-p-tolyl the aminophenyl) -3- phenyl-propanes of=1,1-), BDTAPVB (= Bis- [2- [4- [N, N- bis- (p-methylphenyl) amino] phenyl] vinyl] benzene of Isosorbide-5-Nitrae -), (=N, N, N', N'- tetra--are to toluene by TTB Base -4,4'- benzidine), TPD (bis- [N-3- the aminomethyl phenyl]-N- phenyl aminos of=4,4'-) biphenyl), N, N, N', N'- tetra- 4,4 " '-diaminostilbene of phenyl-, 1', 4', 1 ", 4 ", 1 " '-quaterphenyl, and the tertiary amine with carbazole unit, such as TCTA (= Bis- [4- (9H- carbazole -9- base) phenyl] aniline of 4- (9H- carbazole -9- base)-N, N-).It is also preferred that according to US 2007/ The six azepine terphenyls fork compound and phthalocyanine derivates (such as H of 0092755 A1₂Pc, CuPc (=copper phthalocyanine), CoPc, NiPc、ZnPc、PdPc、FePc、MnPc、ClAlPc、ClGaPc、ClInPc、ClSnPc、Cl₂SiPc、(HO)AlPc、(HO) GaPc、VOPc、TiOPc、MoOPc、GaPc-O-GaPc)。

The triarylamine compound of particularly preferred following formula (TA-1) to (TA-6), is disclosed in document EP 1162193 B1, EP 650 955 B1, Synth.Metals (synthesis metal) 1997,91 (1-3), 209, DE 19646119 A1, WO 2006/122630 A1, EP 1 860 097 A1, EP 1834945 A1, JP 08053397 A, US 6251531 B1, US 2005/0221124, JP 08292586 A, US 7399537 B2, US 2006/0061265 A1, EP 1 661 888 and WO In 2009/041635.The compound of the formula (TA-1) to (TA-6) can be also substituted:

The other compounds or group or structural unit that may be used as hole-injecting material be described in 0891121 A1 of EP and In 1029909 A1 of EP, and implanted layer is generally described in 2004/0174116 A1 of US.

Preferably, these arylamines and heterocyclic compound for being typically used as hole injection and/or hole mobile material cause HOMO is greater than -5.8eV (relative to vacuum level), more preferably greater than -5.5eV.

Compound or group or structural unit with electron injection and/or electron transport property are such as pyridines, pyrimidine, Pyridazine, pyrazine,Diazole, quinoline, quinoxaline, anthracene, benzanthracene, pyrene, benzimidazole, triazine, ketone, phosphine oxide and azophenlyene spread out Biology and triarylborane and it is other with low level LUMO (LUMO=lowest unoccupied molecular orbital) containing the miscellaneous of O, S or N Cycle compound.

Specially suitable compound or group or structural unit for electron-transport and electron injecting layer are 8- hydroxyl quinolines Metallo-chelate (such as LiQ, AlQ of quinoline₃、GaQ₃、MgQ₂、ZnQ₂、InQ₃、ZrQ₄), BAlQ, Ga8- oxyquinoline complex compound, 4- aza-phenanthrenes -5- alcohol Be complex compound (5529853 A of US, referring to formula ET-1), butadiene derivatives (US 4356429), heterocycle Optical Bleaching Agent (US 4539507), benzimidizole derivatives (2007/0273272 A1 of US), such as TPBI (US 5766779, referring to formula ET-2), 1,3,5-triazines, such as two fluorenes of spiral shell-pyrrolotriazine derivatives (such as according to DE 102008064200), pyrene, anthracene, aphthacene, fluorenes, spiro fluorene, dendritic macromole, aphthacene (such as rubrene derivative), 1, 10- phenanthroline derivative (JP 2003-115387, JP 2004-311184, JP-2001-267080, WO 2002/043449), Silole derivative (EP 1480280, EP 1478032, EP 1469533), borane derivative, such as three containing Si Aryl borane derivative (2007/0087219 A1 of US, referring to formula ET-3), pyridine derivate (JP 2004-200162), cough up by phenanthrene Quinoline, especially 1,10- phenanthroline derivative, such as BCP and Bphen, including what is connected via xenyl or other aromatic groups A variety of phenanthroline (US-2007-0252517 A1) or phenanthroline (the US 2007-0122656 A1, referring to formula connected by anthracene ET-4 and ET-5).

Equally suitable is heterocyclic organic compounds or group or structural unit, such as thiopyrandioxide,Azoles, three Azoles, imidazoles orDiazole.Using the pentacyclic example including N, such asAzoles, preferably 1,3,4-Diazole, such as formula ET-6, The compound of ET-7, ET-8 and ET-9 are especially specified in 2007/0273272 A1 of US；Thiazole,Diazole, thiadiazoles, Triazole, referring particularly to US 2008/0102311 A1 and Y.A.Levin, M.S.Skorobogatova, Khimiya Geterotsiklicheskikh Soedinenii 1967 (2), 339-341, the compound of preferred formula ET-10, silicon Polymorphs Diene derivatives.Preferred compound is following formula (ET-6) to (ET-10):

Organic compound or group or structural unit, such as Fluorenone, fluorenes subunit methane, tetra-carbonic, anthraquinone also can be used Bismethane, diphenylquinone, anthrone and anthraquinone diethylene triamine derivative.

The anthracene (passing through 1- naphthalene or 2- naphthalene and 4- xenyl or 3- xenyl) or contain that preferably 2,9,10- replaces Molecule (2008/0193796 A1 of US, referring to formula ET-11) of two anthracene units.Furthermore very advantageously 9,10- replace Anthracene unit and benzimidizole derivatives compound (US 1551206 A1 of 2,006 147747 A and EP, referring to formula ET-12 and ET-13)。

Preferably, the compound or group or structural unit that can produce electron injection and/or electron transport property cause LUMO is less than -2.5eV (relative to vacuum level), more preferably less than -2.7eV.

Mixture of the invention may include illuminator, in this case according to the present invention available compound OSM1 and OSM2 is configurable to illuminator.Term " illuminator " refers to such material, can pass through any kind of energy of transfer After measuring the excitation realized, so that radiation transistion is to ground state and shines.In general, there are two types of the illuminators of known class: fluorescence And phosphorescent emitter.Term " fluorescent illuminant " refer to the material that wherein there is radiation transistion from excited singlet state to ground state or Compound.Term " phosphorescent emitter " preferably refers to luminescent material or compound comprising transition metal.

If dopant causes above-mentioned characteristic in system, illuminator is also commonly referred to as dopant.Include host material Refer to the component in mixture with small percentage with the dopant in the system of dopant.Correspondingly, comprising host material and Host material in the system of dopant refers to the component in mixture with larger proportion.Therefore, term " phosphorescent emitter " It can also for example refer to phosphorescent dopants.

The compound or group or structural unit that can be shone include fluorescent illuminant and phosphorescent emitter.These include tool Have Stilbene, Stilbene amine, styrylamine, cumarin, rubrene, rhodamine, thiazole, thiadiazoles, cyanine, thiophene, to benzene subunit, phthalein Cyanines, porphyrin, ketone, quinoline, imines, anthracene and/or pyrene structure compound.It particularly preferably can be even at room temperature with efficient Rate shines from triplet, that is, shows the compound of electroluminescent phosphorescence rather than electroluminescent fluorescent, typically results in energy efficiency increase.It is suitable Together in this purpose be first containing atomic number greater than 36 heavy atom compound.Preferred compound is above-mentioned containing meeting The compound of the d or f transition metal of condition.Herein particularly preferably containing the 8th to 10 race's element (Ru, Os, Rh, Ir, Pd, Pt respective compound).Functional compounds useful herein include for example a variety of complex compounds, such as in such as WO 02/068435 02/081488 A1, EP 1239526 of A1, WO is described in A2 and 2004/026886 A2 of WO.

The hereinafter preferred compound that may be used for fluorescent illuminant that citing is described in detail.Preferred fluorescent illuminant choosing Classification is descended freely: single styryl amine, diphenylethyllene amine, triphenylethylene base amine, tetraphenyl ethylene base amine, styryl phosphine, benzene Vinyl ethers and arylamine.

Single styryl amine refers to preferred at least one containing a substituted or unsubstituted styryl group The compound of ground aromatic amine.Diphenylethyllene amine refers to containing there are two substituted or unsubstituted styryl group and at least The compound of one preferably aromatic amine.Triphenylethylene base amine refers to containing there are three substituted or unsubstituted styryl bases The compound of group and at least one preferably aromatic amine.Tetraphenyl ethylene base amine refers to containing there are four substituted or unsubstituted benzene The compound of vinyl groups and at least one preferably aromatic amine.The styryl group is more preferably Stilbene, can also have It is further substituted with.To define corresponding phosphine and ether in a manner of as amine.Arylamine or aromatics in the context of the present invention Amine refers to containing there are three be bound directly to the substituted or unsubstituted aromatics of nitrogen or the compound of heteroaromatic ring system.It is preferred that Ground, at least one of these aromatics or heteroaromatic ring system are condensed ring systems preferably at least 14 aromatic ring atoms.This A little preferred embodiments is aromatics anthranylamine, aromatics anthradiamine, aromatics pyrene amine, aromatics pyrene diamines, aromatics lettuce amine or aromatics lettuce diamines.Virtue Race's anthranylamine refers to the compound that one of diarylamino groups are directly preferably bonded at 9 with anthryl group.Aromatics anthradiamine Refer to two of them diarylamino groups directly with anthryl group preferably in 2,6 or 9,10 compounds being bonded.With with this Similar mode defines pyrene amine, pyrene diamines, lettuce amine and the lettuce diamines of aromatics, wherein the diarylamino groups are preferably at 1 Or 1,6 be bonded with pyrene.

Other preferred fluorescent illuminants are selected from indeno fluorenamine or indeno fluorenediamine, are especially specified in document WO 06/ In 122630；Benzo indeno fluorenamine or benzo indeno fluorenediamine, are especially specified in document WO 2008/006449；And hexichol And indeno fluorenamine or dibenzo indeno fluorenediamine, it is especially specified in document WO 2007/140847.

The example of the compound from styryl amine or group or structural unit that may be used as fluorescent illuminant is Substituted or unsubstituted three Stilbene amine is described in WO 06/000388, WO 06/058737, WO 06/000389, WO 07/ Dopant in 065549 and WO 07/115610.Diphenylethyllene benzene and distyrylbiphenyl derivatives are described in US In 5121029.Other styryl amine are found in 2007/0122656 A1 of US.

Particularly preferred styrylamine compounds are the compounds and DE of formula EM-1 described in 7250532 B2 of US The compound of formula EM-2 described in 10 2,005 058557 A1:

Particularly preferred triarylamine compound or group or structural unit are 1583691 A, JP 08/ of document CN 053397 A and US 6251531 B1, EP 1957606 A1, US 2008/0113101 A1, US 2006/210830 A, WO The compound and its derivative for the formula EM-3 to EM-15 being described in detail in 08/006449 and DE 102008035413:

The other preferred compounds or group or structural unit that may be used as fluorescent illuminant are selected from naphthalene, anthracene, aphthacene, benzene And anthracene, benzophenanthrene (DE 10 2,009 005746), fluorenes, fluoranthene, two indenos, indeno, phenanthrene, (US 2007/0252517 A1), pyrene, lettuce, decacyclene, coronene, tetraphenyl cyclopentadiene, Pentaphenylcyclopentadiene, fluorenes, spiro fluorene, rubrene, cumarin (US 4769292, US 6020078,2007/0252517 A1 of US), pyrans,Azoles, benzoAzoles, benzothiazole, benzo miaow Azoles, pyrazine, cinnamate, diketopyrrolo-pyrrole, acridone and quinacridone (2007/0252517 A1 of US) derivative.

In anthracene compound, the anthracene particularly preferably replaced at 9,10, such as 9,10- diphenylanthrancene and 9,10- is bis- (phenylene-ethynylene) anthracene.Bis- (the 9'- acetenyl anthryl) benzene of 1,4- are also preferred dopant.

It is also preferred that rubrene, cumarin, rhodamine, quinacridone such as DMQA (=N, N'- dimethyl quinacridine Ketone), dicyano first subunit pyrans such as DCM (=4- (dicyano second subunit) -6- (4- dimethylamino-styryl -2- first Base) -4H- pyrans), thiapyran, polymethine, pyransAnd thiapyranThe derivative of salt, two indenos and indeno.

Blue luminescence body is preferably polynuclear aromatic compound, such as 9, and 10- bis- (2- naphthyl anthracene) and other anthracenes are derivative Object, aphthacene derivative, xanthene, such as 2,5,8,11- tetra-terts, benzene subunit, such as 4, the bis- (9- ethyl -3- of 4'- Carbazole ethylene subunit) -1,1'- biphenyl, fluorenes, fluoranthene, aryl pyrene (2006/0222886 A1 of US), fragrant subunit ethylene subunit (US 5121029, US 5130603), bis- (azine) imines boron compounds (2007/0092753 A1 of US), bis- (azine) first Asias Based compound and quinoline-2-ketone compound.

Other preferred blue luminescence bodies are described in C.H.Chen etc.: " Recent developments in Organic electroluminescent materials " Macromol.Symp. (macromolecular seminar), 125, (1997) 1-48 and " Recent progress of molecular organic electroluminescent materials and Devices " Mat.Sci.and Eng.R (Materials Science and Engineering report), 39 (2002), in 143-222.

Other preferred blue luminescence bodies are hydrocarbon disclosed in DE 102008035413.It is also especially preferred that The compound being described in detail in WO 2014/111269, especially with the compound of bis- (indenofluorene) basic frameworks.For disclosed Purpose, above-mentioned document DE 102008035413 and 2014/111269 A2 of WO are incorporated by reference into the application.

Hereinafter citing details the preferred compound that may be used as phosphorescent emitter or group or structural unit.

The example of phosphorescent emitter is found in WO 00/70655, WO 01/41512, WO 02/02714, WO 02/ 15645, in EP 1191613, EP 1191612, EP 1191614 and WO 05/033244.In general, according to the prior art Sum all phosphorescent complexes known to the technical staff of field of organic electroluminescence for phosphorescent OLED are all suitable, and And those skilled in the art will use other phosphorescent complexes in the case where not making the creative labor.

Phosphorescent metal complex preferably comprises Ir, Ru, Pd, Pt, Os or Re.

Preferred ligand is 2- phenylpyridine derivative, 7,8- benzoquinoline derivative, 2- (2- thienyl) pyridine derived Object, 2- (1- naphthalene) pyridine derivate, 1- octaverine, 3- octaverine or 2- phenylchinoline are derivative Object.All these compounds can be substituted, such as be replaced by fluorine, cyano and/or trifluoromethyl substituent for blue light.Auxiliary is matched Body is preferably acetylacetonate or pyridine carboxylic acid.

What it is particularly suitable as illuminator is the Pt or Pd of formula EM-16 and the complex compound of tetradentate ligands.

The compound of formula EM-16 is described in greater detail in 2007/0087219 A1 of US, in order to explain taking in above formula Dai Ji and label refer to the document for disclosure purposes.

In addition suitably there is the Pt- porphyrin complex (2009/0061681 A1 of US) for expanding ring system and Ir complexing Object, such as 2,3,7,8,12,13,17,18- octaethyl -21H, 23H- porphyrin-Pt (II),-four benzo porphin of tetraphenyl-Pt (II) Quinoline (2009/0061681 A1 of US), cis--bis- (2- phenylpyridine root conjunction-N, C^2') Pt (II), cis--bis- (2- (2'- thiophene Base) pyridine root conjunction-N, C^3') Pt (II), cis--bis- (2- (2'- thienyl) quinoline root conjunction-N, C^5') Pt (II), (2- (4,6- bis- Fluorophenyl) pyridine root conjunction-N, C^2') Pt (II) acetylacetonate or three (2- phenylpyridine root conjunction-N, C^2') Ir (III) (=Ir (ppy)₃, green light), bis- (2- phenylpyridine root conjunction-N, C²) Ir (III) acetylacetonate (=Ir (ppy)₂Acetylacetonate Object, green light, US 2001/0053462 A1, Baldo, Thompson etc., Nature (nature), 403, (2000), 750-753), Bis- (1- phenyl isoquinolin quinoline root conjunction-N, C^2') (2- phenylpyridine root conjunction-N, C^2') iridium (III), it is bis- (2- phenylpyridine root conjunction-N, C^2') (1- phenyl isoquinolin quinoline root conjunction-N, C^2') iridium (III), bis- (2- (2'- benzothienyl) pyridine root conjunction-N, C^3') iridium (III) Acetylacetonate, pyridine carboxylic acid bis- (2- (4', 6'- difluorophenyl) pyridine root conjunction-N, C^2') iridium (III) (FIrpic, blue light), Four (1- pyrazolyl) boric acid bis- (2- (4', 6'- difluorophenyl) pyridine root conjunction-N, C^2') Ir (III), three (2- (biphenyl -3- base) - 4- tert .-butylpyridine) iridium (III), (ppz)₂Ir(5phdpym)(US 2009/0061681 A1)、(45ooppz)₂Ir (5phdpym) (2009/0061681 A1 of US), the derivative of 2- phenylpyridine-Ir complex compound, such as PQIr (=bis- (2- benzene Base quinolyl-N, C^2') acetylacetonate iridium (III)), it is three (2- phenyl isoquinolin quinoline root conjunction-N, C) Ir (III) (feux rouges), double (2- (2'- benzo [4,5-a] thienyl) pyridine root conjunction-N, C³) Ir acetylacetonate ([Btp₂Ir (acac)], feux rouges, Adachi etc., Appl.Phys.Lett. (applied physics flash report), 78 (2001), 1622-1624).Furthermore it is particularly suitable to The complex compound being described in detail in WO 2016/124304.Cited documents above, especially 2016/124304 A1 of WO, for open Purpose be incorporated by reference into the application.

That equally suitable is trivalent lanthanide series such as Tb³⁺And Eu³⁺Complex compound (J.Kido etc., Appl.Phys.Lett. (applied physics flash report), 65 (1994), 2124；Kido etc., Chem.Lett. (Chemistry Letters), 657,1990；2007/0252517 A1 of US) or Pt (II), Ir (I), Rh (I) and two mercaptan of succinonitrile phosphorescent complexes (Johnson etc., JACS 105,1983,1795) ,-three carbonyl diimine complex compound of Re (I) (especially Wrighton, JACS 96, 1974,998), (Ma etc., Synth.Metals (are closed the complex compound of Os (II) and cyano ligand and bipyridyl or phenanthroline ligand At metal), 94,1998,245).

Other phosphorescent emitters with tridentate ligand are described in US 6824895 and US 10/729238.It glows Phosphorescent complexes are disclosed in US 6835469 and US 6830828.

The particularly preferred compound or group or structural unit that may be used as phosphorescent dopants include US 2001/ 0053462 A1 and Inorg.Chem. (inorganic chemistry), 2001,40 (7), 1704-1711；JACS 2001,123(18), Formula EM-17 compound and its derivative described in 4304-4312.

Derivative is described in 7378162 B2, US 6835469 of US in B2 and 2003/253145 A of JP.

In addition, the 7238437 formula EM-18 to EM- described in A1 and EP 1348711 of B2, US 2009/008607 of US 21 compound and its derivative may be used as illuminator.

Quantum dot may also serve as illuminator, these materials are disclosed in detail in 2011/076314 A1 of WO.

The compound or group or structural unit for being especially used as material of main part together with luminophor include from more The material of a classification.

Material of main part usually has the biggish band gap between HOMO and LUMO compared to luminiferous material used.This Outside, preferred material of main part shows the characteristic of hole transport or electron transport material.In addition, material of main part can have electronics Transmission or hole transporting properties.

Material of main part is also referred to as host material in some cases, especially in material of main part and phosphorescent emitter in OLED In when being applied in combination situation it is such.

The preferred material of main part being especially used together with fluorescent dopants or total material of main part classification chosen from the followings: Oligomeric virtue subunit (such as 2,2', 7,7'- tetraphenyl spiral shell, two fluorenes or dinaphthyl anthracene according to EP 676461), especially containing thick Close the oligomeric fragrant subunit of aromatic group, such as anthracene, benzanthracene, benzophenanthrene (DE 10 2,009 005746, WO 2009/ 069566), phenanthrene, aphthacene, coronene, lettuce, fluorenes, spiro fluorene, phthalein simultaneously, naphtho-, decacyclene, rubrene, oligomeric virtue is sub- Base ethylene subunit (such as bis- (2,2- the diphenylacetylene) -1,1'- biphenyl of DPVBi=4,4'- or spiral shell-according to EP 676461 DPVBi), the metal complex of polypody metal complex (such as according to WO 04/081017), especially 8-hydroxyquinoline, such as AlQ₃(=tri- (8-hydroxyquinoline) aluminium (III)) or bis- (conjunction of 2- methyl -8- quinoline root)-(4- phenylphenoxy) aluminium, including with The chelate (2007/0092753 A1 of US) and quinoline-metal complex of imidazoles, aminoquinoline metal complex, benzo quinoline Quinoline metal complex, hole-conductive compound (such as according to WO 04/058911), electronics conducting compound, especially ketone, oxygen Change (such as according to WO 05/084081 and WO 05/084082) such as phosphine, sulfoxide, carbazole, spiral shell carbazole, indeno carbazoles, resistance turns isomery Body (such as according to WO 06/048268), boronic acid derivatives (such as according to WO 06/117052) or benzanthracene (such as according to WO 08/145239)。

It may be used as material of main part or the altogether particularly preferred compound of material of main part or group or structural unit be selected from such as Under classification: the atropisomer of oligomeric fragrant subunit or these compounds comprising anthracene, benzanthracene and/or pyrene.In the present invention Oligomeric fragrant subunit hereinafter refers to the compound that wherein at least three aryl or fragrant subunit group bond together.

Preferred material of main part is especially selected from the compound of formula (H-100),

Ar⁵-(Ar⁶)_p-Ar⁷ (H-100)

Wherein Ar⁵、Ar⁶、Ar⁷It is identical or different in each case and be with 5 to 30 aromatic ring atoms and can Optionally substituted aryl or heteroaryl group, and p is the integer in 1 to 5 range；Meanwhile the Ar as p=1⁵、Ar⁶With Ar⁷In pi-electron summation be at least 30, and be at least 36 as p=2, and be at least 42 as p=3.

It is highly preferred that in the compound of formula (H-100), Ar⁶Group is anthra and Ar⁵And Ar⁷Group is in 9 and 10 Bonding, wherein these groups can be optionally substituted.Most preferably, Ar⁵And/or Ar⁷At least one of group is fused-aryl base Group, selected from 1- naphthalene or 2- naphthalene, 2- phenanthryl, 3- phenanthryl or 9- phenanthryl or 2- benzo anthryl, 3- benzo anthryl, 4- benzo Anthryl, 5- benzo anthryl, 6- benzo anthryl or 7- benzo anthryl.Compound based on anthracene is described in 2007/0092753 A1 of US In 2007/0252517 A1 of US, for example, 2- (4- aminomethyl phenyl) -9,10- bis- (2- naphthalene) anthracene, 9- (2- naphthalene) -10- (1, 1'- biphenyl) anthracene and bis- [4- (2,2- diphenylacetylene) phenyl] anthracenes of 9,10-, 9,10- diphenylanthrancene, bis- (the phenyl second of 9,10- Alkynyl) anthracene and bis- (the 9'- acetenyl anthryl) benzene of 1,4-.It is also preferable that there are two the compound (US 2008/ of anthracene unit for tool 0193796 A1), such as 10, bis- [1,1', 4', 1 "] terphenyl -2- base -9, the 9'- dianthranides of 10'-.

Other preferred compounds are the derivatives of following substance: arylamine, styryl amine, fluorescein, diphenyl fourth Diene, tetraphenylbutadiene, cyclopentadiene, tetraphenyl cyclopentadiene, Pentaphenylcyclopentadiene, cumarin,Diazole, double benzosOxazoline,Azoles, pyridine, pyrazine, imines, benzothiazole, benzoAzoles, benzimidazole (2007/0092753 A1 of US) are for example 2,2', 2 "-(1,3,5- benzene subunit) three [1- phenyl -1H- benzimidazole], aldazine, Stilbene, styryl virtue ylidene derivatives example Such as bis- [4- (2, the 2- diphenylacetylene) phenyl] anthracenes of 9,10- and diphenylethyllene virtue ylidene derivatives (US 5121029), two Phenylethylene, vinyl anthracene, diaminocarbazole, pyrans, thiapyran, diketopyrrolo-pyrrole, polymethine, cinnamate and fluorescence dye Material.

The particularly preferably derivative of arylamine and styryl amine, such as the TNB (bis- [N- (1- naphthalene)-of=4,4'- N- (2- naphthalene) amino] biphenyl).Metal -8-hydroxyquinoline complex compound such as LiQ or AlQ₃It may be used as total main body.

The compound preferably with oligomeric fragrant subunit or group or structural unit as matrix are specified in US 2003/ 0027016 A1、US 7326371 B2、US 2006/043858 A、WO 2007/114358、WO 08/145239、JP 3148176 B2、EP 1009044、US 2004/018383、WO 2005/061656 A1、EP 0681019B1、WO 2004/ In 013073A1, US 5077142, WO 2007/065678 and DE 102009005746, particularly preferred formula H- 102 to H-108 descriptions.

Furthermore, it is possible to which the compound or group or structural unit that are used as main body or matrix include making together with phosphorescent emitter Material.These compounds or group or structural unit for the structural unit being also used as in polymer include CBP (N, N- Double carbazyl biphenyl), carbazole derivates (such as according to WO 05/039246, US 2005/0069729, JP 2004/288381, EP 1205527 or WO 08/086851), azepine carbazole (such as according to EP 1617710, EP 1617711, EP 1731584 or JP 2005/347160), ketone (such as according to WO 04/093207 or according to DE 102008033943), phosphine oxide, sulfoxide and sulfone (such as according to WO 05/003253), oligocene subunit, aromatic amine (such as according to US 2005/0069729), bipolarity matrix Material (such as according to WO 07/137725), silane (such as according to WO 05/111172), 9,9- diaryl fluorene derivatives (such as According to DE 102008017591), azepine boron heterocyclic pentylene or borate (such as according to WO 06/117052), triazine derivatives Object (such as according to DE 102008036982), indolocarbazole derivatives (such as according to WO 07/063754 or WO 08/ 056746), indenocarbazole derivatives (such as according to DE 102009023155 and DE 102009031021), diaza phosphorus heterocycle Pentadiene derivant (such as according to DE 102009022858), triazole derivative,Azoles andZole derivatives, imdazole derivatives, Polyaromatic alkane derivatives, pyrazoline derivative, pyrazolone derivative, distyrylpyrazine derivatives, thiapyran dioxy Compound derivative, phenylenediamine derivative, aromatic uncle amine, styryl amine, the chalcone derivative that amino replaces, indoles, hydrazone spread out Biology, stilbene derivative, silazane derivatives, aromatics diformazan ylidene compounds, carbodiimide derivative, 8-hydroxyquinoline are derivative The metal complex of object such as AlQ₃, the also 8-hydroxyquinoline complex compound (US 2007/ containing triaryl amino-phenol ligand 0134514 A1), metal complex polysilane compound and thiophene, benzothiophene and dibenzothiophene derivatives.

The example of preferred carbazole derivates be mCP (bis- carbazole benzene of=1,3-N, N- (=9,9'- (1,3- benzene subunit) is double- 9H- carbazole)) (formula H-9), CDBP (=9,9'- (2,2'- dimethyl [1,1'- biphenyl] -4,4'- diyl) double -9H- carbazoles), 1, Bis- (bis- carbazole of N, the N'-) benzene of 3- (bis- (carbazole -9- base) benzene of=1,3-), PVK (polyvinyl carbazole), 3,5- bis- (9H- carbazoles - 9- yl) biphenyl and CMTTP (formula H10).Particularly preferred compound is specified in US 2007/0128467 A1 and US 2005/ (formula H-111 is into H-113) by 0249976 A1.

Preferred tetra- aryl compound of Si- is for example specified in document US 2004/0209115, US 2004/0209116, US 2007/0087219 A1 and H.Gilman, E.A.Zuech, Chemistry&Industry (chemistry and industry) (Britain's human relations Earnestly), in 1960,120.Particularly preferred tetra- aryl compound of Si- is described by formula H-114 to H-120.

The particularly preferred compound or group or structural unit for being used to prepare the matrix of phosphorescent dopants are especially specified in DE 102009022858, DE 102009023155, in EP 652273 B1, WO 07/063754 and WO 08/056746, it is special Not preferred formula H-121 to H-124 description.

About the functional compounds available according to the present invention or group or structural unit that may be used as material of main part, especially Preferably with the substance of at least one nitrogen-atoms.These preferably include aromatic amine, pyrrolotriazine derivatives and carbazole derivates.Example Such as, carbazole derivates especially show surprising high efficiency.Pyrrolotriazine derivatives unexpectedly cause comprising mentionedization Close the long-life of the electronic device of object.

Furthermore preferably using a variety of different host materials for being in form of mixtures, especially at least a kind of electronics conduction Host material and at least one hole-conductive host material.It is also preferred that transmitting host material and electrically inert base using charge The mixture of material (even if electrically inert host material participates in but not significantly participates in charge transmission), such as in such as WO 2010/ Described in 108579.

In addition, the transition improved from singlet state to triplet can be used and have the function of illuminator characteristic for carrying Compound and improve these compounds phosphorescent characteristics compound or group or structural unit.The unit that can be used for the purpose is outstanding It is carbazole and bridging carbazole dimerization body unit, as described in such as 04/113468 A1 of 04/070772 A2 of WO and WO 's.May be additionally used for the purpose is ketone, phosphine oxide, sulfoxide, sulfone, silane derivative and similar compound, such as in such as WO Described in 05/040302 A1.

N-type dopant in this article refers to reducing agent, i.e. electron donor.The preferred embodiment of n-type dopant is 4 He of W (hpp) According to other electron rich metal complexes of 2005/086251 A2 of WO, P=N compound (such as 2012/175535 A1 of WO, 2012/175219 A1 of WO), naphthylene carbodiimides (such as 2012/168358 A1 of WO), fluorenes (such as WO 2012/ 031735 A1), free radical and diyl (such as 1,837,926 2007/107306 A1 of A1, WO of EP), pyridine (such as EP 2452946 2463927 A1 of A1, EP), N- heterocyclic compound (such as 2009/000237 A1 of WO) and acridine and azophenlyene (such as 2007/145355 A1 of US).

In addition, available compound OSM1 and OSM2 can be configured to wide bandgap material according to the present invention.Wide bandgap material is Refer to the material in the disclosure meaning of US 7,294,849.These systems show particularly advantageous in electroluminescent device Performance data.

Preferably, the compound as wide bandgap material can have 2.5eV or bigger, preferably 3.0eV or bigger, very excellent Select 3.5eV or bigger band gap.A kind of method for calculating band gap is minimum not account for via highest occupied molecular orbital (HOMO) and The energy level of molecular orbit (LUMO).

In addition, available compound OSM1 and OSM2 can be configured to hole barrier materials (HBM) according to the present invention.Hole resistance Obstructing material refers to the material that hole (positive charge) conduction is prevented or minimized in layered composite, especially in the material with neighbour It is even more so when the layer form arrangement of nearly luminescent layer or hole-conductive layer.In general, hole barrier materials are compared to adjacent layer In hole mobile material have lower HOMO energy level.The luminescent layer and electronics that hole blocking layer is usually placed in OLED pass Between defeated layer.

In principle, any of hole barrier materials can be used.In addition to other holes described in the other places of the application Except barrier material, hole barrier materials appropriate are metal complex (US 2003/0068528), such as bis- (2- methyl -8- Quinoline root closes) (4- phenylphenoxy) aluminium (III) (BAlQ).- three (1- Phenylpyrazole root of using face formula same for these purposes Conjunction-N, C2) iridium (III) (Ir (ppz) 3) (2003/0175553 A1 of US).It can also use phenanthroline derivative, such as BCP or phthalimide, such as TMPP.

In addition, hole barrier materials appropriate are described in WO 00/70655 A2, WO 01/41512 and WO 01/93642 In A1.

In addition, available compound OSM1 and OSM2 can be configured to electron-blocking materials (EBM) according to the present invention.Electronics resistance Obstructing material refers to the material that electronics conduction is prevented or minimized in layered composite, especially in the material with neighbouring luminescent layer Or electronic conductive layer layer form arrangement when it is even more so.In general, electron-blocking materials are compared to the electronics in adjacent layer Transmission material has higher lumo energy.

In principle, any of electron-blocking materials can be used.In addition to other electronics of the other place descriptions of the application Except barrier material, electron-blocking materials appropriate are transition metal complex, such as 3 (US 2003/ of Ir (ppz) 0175553)。

The example of suitable inventive mixture is composition described below, and it includes two kinds, three kinds or four kinds to have The compound of formula:

Mixture 1

Mixture 2

Mixture 3

Mixture 4

Mixture 5

Mixture 6

Mixture 7

Mixture 8

It is preferred that feasible situation is, at least two organic functions chemical combination object OSM1 and OSM2 in 1:1 to 100:1, preferably Weight rate within the scope of 1:1 to 10:1 uses, using with highest and lowest ratio being described in constitutional isomer each other The ratio of compound.

Preferably, the similarity of at least two organic functions chemical combination object OSM1 and OSM2 calculated according to Tanimoto exists In the range of 80% to less than 100%, preferably 90% to 99.9% and more preferable 95% to 99.5%.

The preferred embodiment of inventive mixture is specifically described in detail in embodiment, these mixtures can be used alone or with Other compound combinations are used for all purposes of the invention.

As long as meeting condition specified in claim 1, above-mentioned preferred embodiment can be combined with each other as needed. In a particularly preferred embodiment of the invention, above-mentioned preferred embodiment is applicable in simultaneously.

In principle the compound of the present invention can be prepared by a variety of methods.However, method described below has been found to It is specially suitable.

Therefore, the present invention also provides a kind of mixing prepared comprising at least two organic functions chemical combination object OSM1 and OSM2 The method of object, wherein preparing two kinds of organic functions chemical combination object OSM1 and OSM2 by coupling reaction and being mixed or prepared Mixture comprising at least two organic functions chemical combination object OSM1 and OSM2.

Suitable compound OSM1 and OSM2 can be obtained via coupling reaction from known precursor, above-mentioned group, structure Unit and/or substituent group S1 or S2 are bonded by the coupling reaction.

Resulting in the especially suitable and preferred coupling reaction that C-C key is formed and/or C-N key is formed is basis Those of BUCHWALD, SUZUKI, YAMAMOTO, STILLE, HECK, NEGISHI, SONOGASHIRA and HIYAMA.These are anti- It should be widely known, and the embodiment will provide further instruction for those skilled in the art.

The principle of preparation method as detailed above is in principle it is known that and art technology from the document of similar compound Personnel can easily modify the preparation for the compounds of this invention.Other information is found in embodiment.

Can be by these methods, then purifying (such as recrystallization or distillation), obtains high-purity, is preferably greater than when necessary 99% (passes through¹H NMR and/or HPLC measurement) the compounds of this invention comprising formula (I) structure.

The compounds of this invention OSM1 and OSM2 can also have suitable substituent group, such as longer alkyl group (about 4 to 20 A carbon atom), especially branched alkyl group, or the aryl group optionally replaced, such as xylyl, mesitylene base or The terphenyl or tetrad phenyl group of branch, at room temperature with enough concentration standard organic solvent such as butyl benzoate, Dissolubility is generated in 3- phenoxytoluene, toluene or dimethylbenzene, so as to handle the compound from solution.These are solvable Property compound is handled particularly suitable for handling from solution, such as by printing process.

Available compound OSM1 and OSM2 can also be with mixed with polymers according to the present invention.It equally can be by these compounds It is covalently bound in polymer.Replace or reactive using by reactive leaving group such as bromine, iodine, chlorine, boric acid or borate The compound that polymerizable groups such as alkene or oxetanes replace, this is especially feasible.It is corresponding that these may be used as preparation The monomer of oligomer, dendritic macromole or polymer.Oligomeric or polymerization preferably via halogen functional group or boric acid functional group or It is realized via polymerizable groups.In addition it can make crosslinked polymer via this group.The compound of the present invention and polymer can be with The form of crosslinking or uncrosslinked layer uses.

Therefore, the present invention also provides the oligomer comprising one or more constitutional isomers, polymer or dendroids to divide greatly The mixture of son, wherein exist it is one or more from available compound OSM1 and OSM2 according to the present invention to the polymer, The key of oligomer or dendritic macromole.According to the bonded of the structure of the compound, therefore these form oligomer or polymerization The side chain of object is bonded in main chain.The polymer, oligomer or dendritic macromole can be conjugation, partly conjugated Or it is unconjugated.The oligomer or polymer can be linear, branching or dendritic.As described above is identical preferred Repetitive unit of the feature suitable for the compounds of this invention oligomer, dendritic macromole and polymer.

In such a case, it is possible to make according to the present invention available compound OSM1 polymerize to obtain polymer, and making It closes object OSM2 to polymerize to obtain polymer, by corresponding mixed with polymers.In addition, the compound OSM1 and OSM2 can polymerize to obtain Polymer.In addition, a variety of mixtures of available compound OSM1 and OSM2 can polymerize according to the present invention, then mix a variety of Polymer.Preferably, polymer of the invention, oligomer or dendritic macromole include at least two different components, these Component is different in terms of the monomer composition of ingredient OSM1 and OSM2.

In order to prepare the oligomer or polymer, monomer of the invention is made to carry out homopolymerization or be total to other monomer It is poly-.It is preferred that following copolymer, wherein the unit of preferred embodiment described in formula (I) and/or (II) or context is with 0.01 Range to 99.9 moles of % of %, preferably 5 to 90 moles, more preferable 20 to 80 moles of % exists.Properly and preferably form poly- The comonomer for closing object basic framework is selected from fluorenes (such as according to EP 842208 or WO 2000/022026), two fluorenes of spiral shell (such as root According to EP 707020, EP 894107 or WO 2006/061181), to benzene subunit (such as according to WO 92/18552), carbazole (example Such as according to WO 2004/070772 or WO 2004/113468), thiophene (such as according to EP 1028136), dihydro phenanthrene (such as root According to WO 2005/014689), cis and trans indenofluorene (such as according to WO 2004/041901 or WO 2004/113412), ketone (such as according to WO 2005/040302), luxuriant and rich with fragrance (such as according to WO 2005/104264 or WO 2007/017066) or it is a variety of this A little units.The polymer, oligomer and dendritic macromole can also contain other units, such as hole transporting unit, especially It is based on those of triarylamine and/or electron-transport unit.

In addition it is especially envisaged that the compound available according to the present invention characterized by high glass-transition temperature.At this Aspect especially preferably includes the structure of preferred embodiment described in logical formula (I) and/or (II) or context according to this Available compound is invented, measuring its glass transition temperature according to DIN 51005 (2005-08 editions) is at least 70 DEG C, more excellent Select at least 110 DEG C, even more desirably at least 125 DEG C and particularly preferably at least 150 DEG C.

In order to from liquid phase processing available compound according to the present invention, for example, by spin coating or by printing process at Reason, needs the preparation of the compounds of this invention.These preparations may, for example, be solution, dispersion or lotion.For this purpose, may be used It is preferable to use the mixtures of two or more solvents.Suitable and preferred solvent is, for example, toluene, methyl phenyl ethers anisole, ortho-xylene, Meta-xylene or paraxylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, THF, methyl-THF, THP, chlorine Benzene, twoAlkane, phenoxytoluene, especially 3- phenoxytoluene, (-)-fenchone, 1,2,3,5- durol, 1,2,4,5- tetra- Methylbenzene, 1- methyl naphthalene, 2- methylbenzothiazole, 2- phenoxetol, 2-Pyrrolidone, 3- methylanisole, 4- methylbenzene Methyl ether, 3,4- dimethylanisoles, 3,5- dimethylanisoles, acetophenone, α-terpineol, benzothiazole, isoamyl acid phenenyl ester, benzene Butyl formate, isopropylbenzene, cyclohexanol, cyclohexanone, cyclohexyl benzene, decahydronaphthalenes, detergent alkylate, ethyl benzoate, indane, benzene Methyl formate, NMP, p -Methylisopropylbenzene, phenetole, Isosorbide-5-Nitrae-diisopropyl benzene, benzyl ether, diethylene glycol butyl methyl ether, Triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, 3 the third two Alcohol dimethyl ether, tetraethylene glycol dimethyl ether, 2- isopropyl naphthalene, penta benzene, own benzene, heptan benzene, pungent benzene, 1,1- bis- (3,4- dimethyl Phenyl) ethane, the mixture of hexamethyl indane or these solvents.

Therefore, the present invention also provides a kind of preparations, and it includes the sheets of available compound OSM1 and OSM2 according to the present invention Invention mixture and at least one other compound.The other compound may, for example, be solvent, especially above-mentioned molten The mixture of one of agent or these solvents.The other compound can be optionally that at least one is equally used for electronic device In other organic or inorganic compound, such as luminophor, especially phosphorescent dopants and/or other matrix material Material.This other compound is also possible to polymerization.

Therefore, the present invention also provides a kind of compositions, and it includes available compound OSM1's and OSM2 according to the present invention Inventive mixture and at least one other organic functional material.What functional material usually introduced between the anode and cathode Organic or inorganic material.Preferably, the organic functional material is selected from fluorescent illuminant, phosphorescent emitter, display TADF (heat shock Delayed fluorescence living) illuminator, material of main part, electron transport material, electron injection material, hole mobile material, hole injection Material, electron-blocking materials, hole barrier materials, wide bandgap material, p-type dopant and n-type dopant.

In a particular aspects of the invention, the inventive mixture of available compound OSM1 and OSM2 according to the present invention It may be used as illuminator, be preferably used as fluorescent illuminant, illuminator is applied in combination with suitable host material in many cases. In addition, the inventive mixture of available compound OSM1 and OSM2 may be used as host material according to the present invention, it is especially right In the host material of phosphorescent emitter, host material is applied in combination with other host materials in many cases.

Therefore, the invention further relates to a kind of compositions, and it includes at least one compound OSM1 available according to the present invention With the inventive mixture and at least one other host material of preferred embodiment described in OSM2 or context.According to this One particular aspects of invention, the other host material have electron transport property.

The present invention also provides a kind of compositions, and it includes at least one compound OSM1 and OSM2 available according to the present invention Or the inventive mixture of preferred embodiment described in context and at least one wide bandgap material, wide bandgap material refer to Material in the disclosure meaning of US 7,294,849.These systems show abnormal advantageous property in electroluminescent device It can data.

Preferably, the other compound can have 2.5eV or bigger, preferably 3.0eV or bigger, highly preferred 3.5eV or bigger band gap.A kind of method for calculating band gap is minimum not account for via highest occupied molecular orbital (HOMO) and point The energy level of sub-track (LUMO).

Determined via quantum chemistry calculation the molecular orbit of the material, especially highest occupied molecular orbital (HOMO) and Lowest unoccupied molecular orbital (LUMO), energy level and minimum triplet T₁Energy and lowest excited singlet state S₁Energy.For The organic substance without metal is calculated, passes through " ground state/semiempirical/default spin/AM1/ charge 0/ spin singlet state " side first Method carries out Geometrical optimization.Energy balane is realized subsequently, based on the geometry of optimization.This uses " TD-SCF/DFT/ default Spin/B3PW91 " method and " 6-31G (d) " basis set (charge 0, spin singlet state) carry out.For metal-containing compound, via " ground state/Hartree-Fock/ default spin/spin of LanL2MB/ charge 0/ singlet state " method geometry optimization.It is similar to The above-mentioned method about organic substance realizes energy balane, and difference is to use " LanL2DZ " basis set for metallic atom, and right " 6-31G (d) " basis set is used in ligand.HOMO energy level HEh or the LUMO energy measured with Hartree units is obtained from energy balane Grade LEh.This is as follows by cyclic voltammetry measurement calibration with electronic voltmeter for determining HOMO and lumo energy:

HOMO (eV)=((HEh*27.212) -0.9899)/1.1206

LUMO (eV)=((LEh*27.212) -2.0041)/1.385

In the context of this application, these values are considered as the HOMO and lumo energy of the material.

Minimum triplet T₁It is defined as with the triplet energy from the obvious minimum energy of the quantum chemistry calculation Amount.

Lowest excited singlet state S₁It is defined as with the excitation from the obvious minimum energy of the quantum chemistry calculation Singlet energy.

Method described herein is unrelated with software package used and provides identical result always.It is common for this purpose The example of program is " Gaussian09W " (Koss Corp.) and Q-Chem 4.1 (Q-Chem company).

The invention further relates to a kind of compositions, and it includes at least one compound OSM1 and OSM2 available according to the present invention Or the inventive mixture and at least one of preferred embodiment described in context are preferably selected from fluorescent illuminant, phosphorescence hair The illuminator of body of light and/or the illuminator of display TADF (hot activation delayed fluorescence), the mixture preferably comprise at least one kind Phosphorescent emitter existing in the form of stereoisomer mixture, preferably with the stereoisomer mixture shape of λ and δ isomers Phosphorescent emitter existing for formula.

Dopant in system comprising host material and dopant refers to the component in mixture with small percentage.Phase Ying Di, the host material in the system comprising host material and dopant refer to the component in mixture with larger proportion.

For preferred phosphorescent emitter (the referred to herein as phosphorus in matrix system, preferably mixed-matrix system Photodopant) it is preferred phosphorescent dopants as specified below.

Term " phosphorescent dopants " is usually covered wherein by spin-forbidden transition, for example from excited triplet state or with more Luminous compound is realized in the state of high-spin quantum number such as quintuplet transition.

Suitable phosphorescent compound (=triplet emitters) especially shines, suitable preferably in visual field hair when energized Light and also containing at least one atomic number be greater than 20, preferably greater than 38 and less than 84, more preferably greater than 56 and less than 80 The compound of atom, especially with the metal of the atomic number.Preferred phosphorescent emitter used be containing copper, molybdenum, tungsten, Rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium compound, the especially compound containing iridium or platinum.Of the invention upper Hereinafter, all luminophors containing above-mentioned metal are considered as phosphorescent compound.

The example of above-mentioned illuminator is found in application WO 00/70655, WO 2001/41512, WO 2002/02714, WO 2002/15645、EP 1191613、EP 1191612、EP 1191614、WO 05/033244、WO 05/019373、US 2005/0258742、WO 2009/146770、WO 2010/015307、WO 2010/031485、WO 2010/054731、WO 2010/054728、WO 2010/086089、WO 2010/099852、WO 2010/102709、WO 2011/032626、WO 2011/066898、WO 2011/157339、WO 2012/007086、WO 2014/008982、WO 2014/023377、WO 2014/094961, WO 2014/094960 and not yet disclosed application EP 13004411.8, EP 14000345.0, EP 14000417.7 with EP 14002623.8.In general, the sum of phosphorescent OLED is used in organic electroluminescent according to the prior art All phosphorescent complexes known to technical staff in field are all suitable, and those skilled in the art will not pay Other phosphorescent complexes are used in the case where creative work out.

Following table lists the clear example of phosphorescent dopants:

This hair comprising at least one compound OSM1 and OSM2 available according to the present invention or above-mentioned preferred embodiment The above compound of bright mixture can be preferably used as the active component in electronic device.Electronic device refers to including anode, yin Any device of pole and at least one layer between anode and cathode, the layer include at least one organic or organic metal Compound.Therefore, electronic device of the invention include anode, cathode and at least one contain it is at least one comprising formula (I) and/or (II) middle layer of the compound of structure.Preferred electronic device is selected from organic electroluminescence device (OLED, PLED), has herein Machine integrated circuit (O-IC), organic field effect tube (O-FET), Organic Thin Film Transistors (O-TFT), organic light-emitting transistor (O-LET), organic solar batteries (O-SC), organic optical detector, organophotoreceptorswith, organic field quenching device (O- FQD), organic electric transducer, light-emitting electrochemical cell (LEC), organic laser diode (O- laser) and organic phasmon Luminescent device (D.M.Koller etc., Nature Photonics (Nature Photonics) 2008,1-4), preferably organic electroluminescent Device (OLED, PLED), especially phosphorescent OLED contain at least one change comprising formula (I) structure at least one layer Close object.Particularly preferably organic electroluminescence device.Active component is usually the organic or nothing introduced between anode and cathode Machine material, such as charge injection, charge transmission or charge blocking material, but especially luminescent material and host material.

A preferred embodiment of the invention is organic electroluminescence device.The organic electroluminescence device includes Cathode, anode and at least one luminescent layer.In addition to these layers, it may also include other layer, such as in each case One or more hole injection layers, hole transmission layer, hole blocking layer, electron transfer layer, electron injecting layer, exciton barrier-layer, Electronic barrier layer, charge generation layer and/or organic or inorganic p/n knot.Meanwhile one or more hole transmission layers can be for example with gold Belong to oxide such as MoO₃Or WO₃Or p-type doping is carried out with (complete) fluorination electron deficient aromatic systems, and/or one or more electronics pass Defeated layer is by n-type doping.Equally can by middle layer introduce two luminescent layers between, these layers have the function of for example exciton blocking with/ Or the charge balance in control electroluminescent device.It should be mentioned, however, that each of these layers need not all exist.

In this case, the organic electroluminescence device, which can contain a luminescent layer or it, can contain multiple hairs Photosphere.If there is multiple luminescent layers, then these preferably have multiple luminescence peaks between 380nm and 750nm in total, with So that total result is white luminous；In other words, in luminescent layer using can fluoresce or phosphorescent a variety of light emitting compounds Object.Particularly preferred Three-tider architecture, wherein three layers are displayed in blue, green and orange or red shine (for basic structure, See, for example, WO 2005/011013), or with the system more than three luminescent layers.The system is also possible to one of them Or multiple layers fluoresce and the phosphorescent mixed system of one or more of the other layer.

In a preferred embodiment of the invention, the organic electroluminescence device contains can be used according to the present invention Compound OSM1 and OSM2 or above-mentioned preferred embodiment inventive mixture as the base in one or more luminescent layers Material, preferably as hole-conductive host material, preferably with another host material, preferably electronics conductive matrix material group It closes.In another preferred embodiment of the invention, the other host material is hole transport compound.Another In a preferred embodiment, the other host material is the compound with big band gap, not aobvious participating in The hole and electron-transport in layer are participated in work degree.Luminescent layer includes at least one luminophor.

It can be mixed with available compound OSM1 and OSM2 according to the present invention or according to the present invention of preferred embodiment The suitable host material that object is applied in combination is aromatic ketone, aromatics phosphine oxide or aromatics sulfoxide or sulfone, such as according to WO 2004/ 013080, WO 2004/093207, WO 2006/005627 or WO 2010/006680, triarylamine, especially monoamine, example As according to WO 2014/015935, carbazole derivates, such as CBP (the bis- carbazyl biphenyl of N, N-) or it is disclosed in WO 2005/ 039246, the carbazole in US 2005/0069729, JP 2004/288381, EP 1205527 or WO 2008/086851 is derivative Object, indolocarbazole derivatives, such as according to WO 2007/063754 or WO 2008/056746, indenocarbazole derivatives, Such as according to WO 2010/136109 and WO 2011/000455, azepine carbazole derivates, such as according to EP 1617710, EP 1617711, EP 1731584, JP 2005/347160, bipolarity host material, such as according to WO 2007/137725, Silane, such as according to WO 2005/111172, azepine boron heterocyclic pentylene or borate, such as according to WO 2006/117052 , pyrrolotriazine derivatives, such as according to WO 2010/015306, WO 2007/063754 or WO 2008/056746, zinc complexing Object, such as according to EP 652273 or WO 2009/062578, diaza Silole or four azepine Siloles Derivative, such as according to WO 2010/054729, diaza phosphene derivative, such as according to WO 2010/ 054730, bridging carbazole derivates, such as according to US 2009/0136779, WO 2010/050778, WO 2011/ 042107, WO 2011/088877 or WO 2012/143080, terphenyl pitch derivative, such as according to WO 2012/048781 , lactams, such as according to WO 2011/116865, WO 2011/137951 or WO's 2013/064206 or 4- spiral shell carbazole Derivative, such as apply for EP's 14002104.9 according to WO 2014/094963 or not yet disclosed.With shorter than practical illuminator The luminous other phosphorescent emitter of wavelength equally can be used as total main body and be present in mixture.

Preferably material of main part is triarylamine derivatives altogether, and especially monoamine, indenocarbazole derivatives, 4- spiral shell carbazole spread out Biology, lactams and carbazole derivates.

It will also be preferred a variety of different host materials in form of mixtures, especially at least a kind of electronics conducts base Material and at least one hole-conductive host material.It is not shown again preferably with charge transmission host material and participating in The mixture for participating in the electrically inert host material of charge transmission is write, as described in such as WO 2010/108579.

Further preferably use the mixture of two or more triplet emitters and matrix.In this case, have There are the triplet emitters compared with shortwave luminescent spectrum to be used as the co-substrate with the triplet emitters compared with long wave luminescent spectrum.

It is highly preferred that in one preferred embodiment, can be used compound OSM1 available according to the present invention and The inventive mixture of OSM2 is as the host material in the luminescent layer of organic electronic device, especially in organic electroluminescence Situation in part is in this way, for example situation is such in OLED or OLEC.In this case, according to the present invention may be used containing at least one The host material of the inventive mixture of preferred embodiment described in compound OSM1 and OSM2 or context and a kind of Or a variety of dopants, preferably phosphorescent dopants combination are present in electronic device.

Ratio of the host material in luminescent layer is in this case 50.0 volume % to 99.9 for fluorescent light-emitting layer Volume %, preferably 60.0 volume % to 99.5 volume % and more preferably 92.0 volume % to 99.5 volume %, and for It is 60.0 volume % to 70.0 volume % and the phosphorus for shining in blue region in the luminous phosphorescent layer of green or red area Photosphere is 90.0 volume % to 97.0 volume %.

Correspondingly, the ratio of dopant is 0.1 volume % to 50.0 volume %, preferably 0.5 body for fluorescent light-emitting layer Product % to 20.0 volume % and more preferably 0.5 volume % to 8.0 volume %, and the phosphorescence for shining in blue region is sent out Photosphere is 3.0 volume % to 10.0 volume % and for being 30.0 volume % in the luminous phosphorescence luminescent layer of green or red area To 40.0 volume %.

The luminescent layer of organic electroluminescence device also may include containing there are many host material (mixed-matrix system) and/or more The system of kind dopant.Equally, in this case, the dopant is usually to have those of small percentage material in system Expect and the host material is in system with those of larger proportion material.However, on rare occasion, single matrix Ratio of the material in system is smaller than the ratio of single dopant.

In another preferred embodiment of the invention, according to the present invention available compound OSM1 and OSM2 or on The inventive mixture of preferred embodiment described below is used as the component of mixed-matrix system.The mixed-matrix system Two or three of different host material is preferably comprised, more preferable two different host materials.Preferably, in such case Under, two kinds of materials first is that the material with hole transporting properties and another material is the material with electron transport property Material.However, the desired electron-transport and hole transporting properties of mixed-matrix component can also be predominantly or completely combined in In single mixed-matrix component, other mixed-matrix component meets other functions in this case.Two different matrix Material can exist with the ratio of 1:50 to 1:1, preferably 1:20 to 1:1, more preferable 1:10 to 1:1 and most preferably 1:4 to 1:1. It is preferred that using mixed-matrix system in phosphorescent organic electroluminescent device.One of more detailed information about mixed-matrix system A source is application WO 2010/108579.

The present invention also provides such electronic devices, preferably organic electroluminescence device, pass in one or more holes It is big comprising one or more the compounds of this invention and/or at least one oligomer of the invention, polymer or dendroid in conducting shell Molecule, as hole-conductive compound.

The present invention also provides such electronic devices, preferably organic electroluminescence device, and one kind is included in luminescent layer Or a variety of the compounds of this invention and/or at least one oligomer of the invention, polymer or dendritic macromole, as luminousization Object is closed, preferably as fluorescent illuminant, or as host material, is preferably combined with phosphorescent emitter.

Preferred cathode is the metal with low work function, by various metals such as alkaline-earth metal, alkali metal, main group metal Or metal alloy or multilayered structure that lanthanide series (such as Ca, Ba, Mg, Al, In, Mg, Yb, Sm etc.) is constituted.Furthermore suitable It is the alloy being made of alkali or alkaline earth metal and silver, such as the alloy being made of magnesium and silver.In the case of the multi-layer structure, In addition to the metal, it is possible to use other metals with relatively high work function, such as Ag usually make in this case With the combination of metal, such as Mg/Ag, Ca/Ag or Ba/Ag.It can also be introduced preferably between metallic cathode and organic semiconductor The thin middle layer of material with high dielectric constant.The example that can be used for the material of this purpose is alkali metal fluoride or alkaline earth Metal fluoride is but it is also possible to be corresponding oxide or carbonate (such as LiF, Li₂O、BaF₂、MgO、NaF、CsF、Cs₂CO₃ Deng).Be equally applicable to this purpose is organic alkali metal complex compound, such as Liq (oxyquinoline lithium).The thickness degree of this layer Preferably 0.5 to 5nm.

Preferred anode is the material with high work function.Preferably, the anode, which has, is greater than 4.5eV relative to vacuum Work function.Firstly, be suitable for this purpose is to have the metal of high redox potential, such as Ag, Pt or Au.Secondly, It can preferably metal/metal oxide electrode (such as Al/Ni/NiO_x、Al/PtO_x).For some applications, at least one electrode Must be it is transparent or partially transparent, with realize organic material radiation (O-SC) or shine (OLED/PLED, O- laser Device).Preferred anode material is electric conductivity mixed-metal oxides herein.Particularly preferred tin indium oxide (ITO) or indium zinc oxide (IZO).It is then preferred that electric conductivity adulterate organic material, especially electric conductivity doped polymer, such as PEDOT, PANI or these The derivative of polymer.It is then preferred that p-type doping hole mobile material is applied to anode as hole injection layer, in this feelings Suitable p-type dopant is metal oxide, such as MoO under condition₃Or WO₃, or (complete) fluorination electron deficient aromatic systems.Other conjunctions Suitable p-type dopant is HAT-CN (six cyano, six azepine terphenyl fork) or the compound N PD9 from Novaled.This layer letter Injection of the hole into the material with HOMO low HOMO big i.e. based on numerical value is changed.

In other layer, any material that the layer is such as used for according to the prior art, and this field usually can be used Technical staff can be without creative efforts in electronic device by any one of these materials and this hair Bright combination of materials.

The device is connected and is finally hermetically sealed by the correspondingly structuring (according to application), setting, because The service life of these devices can serious curtailment in the presence of water and/or air.

It is then preferred that such electronic device, especially organic electroluminescence device, it is characterised in that from solution for example By spin coating, or by any printing process such as silk-screen printing, flexible version printing, lithographic printing or nozzle print, but it is more excellent LITI (light-initiated thermal imaging, thermal transfer) or ink jet printing are selected, to generate one or more layers.For this purpose, needing can Soluble compound, such as by suitably replacing acquisition.

Above-mentioned document for representation function compound is incorporated by reference into the application for purposes of this disclosure.

These methods are generally known to the skilled in the art and can be by those skilled in the art without difficulty Applied to containing the structure comprising formula (I) and/or (II) or above-mentioned preferred embodiment the compounds of this invention electronic device, Especially organic electroluminescence device.

Electronic device of the invention, especially organic electroluminescence device, are distinguished by compared with the prior art Following astonishing one or more of advantage:

1. according to the present invention the mixture of available compound OSM1 and OSM2 or oligomer, polymer as derived from it or Preferred embodiment described in dendritic macromole or context shows excellent stability in the solution, wherein the solution is compared It can have higher concentration in the solution only comprising available compound OSM1 or OSM2 according to the present invention.

2. according to the present invention the mixture of available compound OSM1 and OSM2 or oligomer, polymer as derived from it or Preferred embodiment described in dendritic macromole or context forms very good, especially very uniform film from solution.

3. according to the present invention the mixture of available compound OSM1 and OSM2 or oligomer, polymer as derived from it or Preferred embodiment described in dendritic macromole or context shows very high stability and leads to have the very long-life Compound.

4. utilizing the mixture of available compound OSM1 and OSM2 according to the present invention or oligomer as derived from it, polymerization Preferred embodiment described in object or dendritic macromole or context, can avoid in electronic device, especially organic electroluminescent Light loss channel is formed in device.Therefore, these devices are characterized in that high PL efficiency and the therefore high EL efficiency of illuminator, with And matrix is to the excellent energy transmission of dopant.

5. according to the present invention the mixture of available compound OSM1 and OSM2 or oligomer, polymer as derived from it or Preferred embodiment described in dendritic macromole or context is distinguished by excellent thermal stability.

6. according to the present invention the mixture of available compound OSM1 and OSM2 or oligomer, polymer as derived from it or Preferred embodiment described in dendritic macromole or context has excellent glass-film formative.

7. containing the mixture of available compound OSM1 and OSM2 according to the present invention or oligomer as derived from it, polymerization Preferred embodiment described in object or dendritic macromole or context especially as wide bandgap material, as fluorescent illuminant or As electronics conduction and/or the electronic device of hole transport material, especially organic electroluminescence device, there is the extraordinary longevity Life.In this case, these compounds especially cause it is low roll-off, i.e. power efficiency of the device under high luminous density is small size Decline.

8. containing the mixture of available compound OSM1 and OSM2 according to the present invention or oligomer as derived from it, polymerization Preferred embodiment described in object or dendritic macromole or context is as fluorescent illuminant or as electrically conductive material, sky The electronic device of cave conductive material and/or material of main part, especially organic electroluminescence device have excellent efficiency.At this Kind in the case of, according to the present invention the mixture of available compound OSM1 and OSM2 or oligomer, polymer as derived from it or Low operating voltage is generated when preferred embodiment described in dendritic macromole or context is in for electronic device.

These above-mentioned advantages are not accompanied by the deterioration of other Electronic Performances.

Mixture of the invention is suitable for electronic device.Electronic device, which refers to, herein contains at least one comprising at least one The device of the layer of organic compound.However, the component can also include inorganic material or completely formed by inorganic material Layer.

Therefore, the present invention also provides mixtures of the invention in electronic device, especially in organic electroluminescence Purposes in part.

The present invention also provides the inventive mixtures and/or this hair of available compound OSM1 and OSM2 according to the present invention Purposes of bright oligomer, polymer or the dendritic macromole in electronic device is used as fluorescent illuminant, phosphorescent emitter Material of main part, electron transport material and/or hole mobile material, be preferably used as phosphorescent emitter material of main part or be used as sky Hole transport materials are used as electron transport material.

The present invention also provides a kind of electronic devices, and it includes at least one aforementioned present invention mixtures.In this case, Electronic device is also applied for above for preferred feature described in compound.It is highly preferred that the electronic device is selected from Organic Electricity Electroluminescence device (OLED, PLED), organic integrated circuits (O-IC), organic field effect tube (O-FET), organic thin-film transistor Manage (O-TFT), organic light-emitting transistor (O-LET), organic solar batteries (O-SC), organic optical detector, organic light sensation Receiver, organic field quenching device (O-FQD), organic electric transducer, light-emitting electrochemical cell (LEC), organic laser diode (O- Laser) and organic phasmon luminescent device (D.M.Koller etc., Nature Photonics (Nature Photonics) 2008, 1-4), preferably organic electroluminescence device (OLED, PLED), especially phosphorescent OLED.

In yet another embodiment of the present invention, organic electroluminescence device of the invention is free of any individual hole Implanted layer and/or hole transmission layer and/or hole blocking layer and/or electron transfer layer, it means that luminescent layer and hole are injected Layer or anode abuts directly against and/or luminescent layer is abutted directly against with electron transfer layer or electron injecting layer or cathode, such as in such as WO Described in 2005/053051.Make in addition, can be used with the same or similar metal complex of metal complex in luminescent layer For the hole transport or hole-injecting material abutted directly against with luminescent layer, as described in such as WO 2009/030981.

In other layers of organic electroluminescence device of the invention, it can be used and appoint according to the prior art is usually used What material.Therefore, those skilled in the art can send out any about organic electroluminescence without creative efforts Material known to optical device is with the inventive mixture of available compound OSM1 and OSM2 according to the present invention or according to preferred reality The mode of applying is applied in combination.

The inventive mixture of available compound OSM1 and OSM2 according to the present invention, when for organic electroluminescence device When middle, usually there is extraordinary performance.Meanwhile other characteristics of organic electroluminescence device, especially efficiency and voltage, together Sample is more preferable or at least suitable.

It should be pointed out that the variation of heretofore described embodiment is covered by the scope of the present invention.Except non-clearly arranging It removes, otherwise any feature disclosed in the present invention, which can be changed to, provides identical purpose or equivalent or similar purpose optional feature. Therefore, unless otherwise stated, otherwise the present invention disclosed in any feature should be regarded as the example of universal serial or be considered as it is equivalent or Similar feature.

Except non-specific feature and/or step are mutually exclusive, otherwise all features of the invention can in any way mutual group It closes.Preferred feature of the invention is especially true.Similarly, the feature of optional combination can individually (and non-combined) use.

In addition, it is to be noted that many features and especially those of the preferred embodiment of the present invention feature itself should regard For a part that is creativeness and should not being only regarded as embodiments of the present invention.For these features, in addition to any mesh Preceding claimed invention or substitution as any invention for currently requiring that protection, can seek independent protective.

Technical teaching disclosed by the invention can be extracted and combine with other embodiments.

The present invention is explained in detail by following embodiment, and is not intended to limit the invention to this.

Those skilled in the art will manufacture this using the details provided without creative efforts Other electronic devices of invention, and therefore implement the present invention in entire scope claimed.

Embodiment

In order to check the stability of solution of isomer mixture, individual substance and isomer mixture are tested in multi-solvents In stability.Solvent for use is, for example, toluene and 3- phenoxytoluene.According to the present invention, individual substance and isomer mixture It is used with the respective material concentration of 10g/l to 40g/.Individual substance and isomer mixture dissolve in a solvent at room temperature, and And after the completion of dissolution, store 36 hours at room temperature.Hereafter, the precipitating of solution is visually inspected.

1. using three kinds of different materials with each other as constitutional isomer.Structure is described in Table 1.

Table 1: the structure of isomers material.

Stability of solution of the research material M1 to M3 in multi-solvents.All material is under stiring at the short time (several seconds To a few minutes) in be completely dissolved in a solvent.FB1 is highly unstable in 3- phenoxytoluene and toluene, therefore small 36 When after under various concentration visible apparent sediment；Referring to table 2.

Table 2: stability of the respective material in different solvents

Study the stability of solution of a variety of isomer mixtures of the invention in multi-solvents.All isomeries of the invention Body mixture is completely dissolved in a solvent within the short time (several seconds to a few minutes) under stiring.Table 3 shows the range estimation of precipitating Inspection result.The all material mixture of constitutional isomer M1, M2 and M3, even if under various concentration, according to the present invention Also all it is stable in multi-solvents, and does not show any precipitating after storing 36 hours at room temperature.Therefore it can incite somebody to action Loose material such as FB1 is combined with constitutional isomer and is stabilized.

Table 3: the stability of isomer mixture of the invention in different solvents, wherein the concentration values indicated with g/l It is related with concentration of the respective material in each solvent, rather than the total concentration in mixture.Material in mixture it is total dense Degree is calculated by blending ratio (such as 80%M1 and 20%M2) used, and the blending ratio is with weight % report.

2) in another embodiment, using two kinds of different materials with each other as constitutional isomer.Structure is described in table 4 In.

Table 4: the structure of isomers material.

Table 5: stability of the respective material in different solvents

Table 6: the stability of isomer mixture of the invention in different solvents

3) stability of solution of the research material M6 and M7 in multi-solvents (about structure, referring to table 7).The material exists It is completely dissolved in a solvent within the short time (several seconds to a few minutes) under stirring.M6 in 3- phenoxytoluene and toluene all very It is unstable, therefore after 36 hours under various concentration it can be seen that apparent sediment；Referring to table 5.M7 is mentioned molten Slightly soluble in agent, and at room temperature after storage 36 hours, even at a low concentration, it can also be seen that apparent sediment.

Table 7: the structure of isomers material.

Table 8: stability of the respective material in different solvents

Study the stability of solution of a variety of isomer mixtures of the invention in multi-solvents.All isomeries of the invention Body mixture is completely dissolved in a solvent within the short time (several seconds to a few minutes) under stiring.Table 6 shows the range estimation of precipitating Inspection result.The material blends of the constitutional isomer M6 and M7 of various concentration are stable according to the present invention in multi-solvents , and any precipitating is not shown after storing 36 hours at room temperature.

Table 9: the stability of isomer mixture of the invention in different solvents.

The manufacture of the OLED of solution processing

In the literature, such as in WO 2004/037887, there are many systems about the OLED based entirely on solution The description made.It is included in WO 2004/058911, equally exists retouching for many manufactures previously with respect to the OLED based on vacuum It states.In the embodiment being discussed below, the layer applied in a manner of based on solution and based on vacuum combines in OLED, therefore from Solution realizes processing until and realizing succeeding layer (hole blocking layer and electron transfer layer) including luminescent layer and from vacuum.Thus Purpose, previously described conventional method match with situation described herein and combine as follows.

The structure of component is as follows:

Substrate

-ITO(50nm)

Hole injection layer (HIL) (20nm)

Hole transmission layer (HTL) (20nm)

Luminescent layer (EML) (60nm)

Hole blocking layer (HBL) (10nm)

Electron transfer layer (ETL) (40nm)

Cathode

Substrate used is the glass plate of the structuring ITO (tin indium oxide) coated with thickness 50nm.In order to preferably locate Reason, with PEDOT:PSS, (it is expensive to congratulate Li Shi purchased from Germany for poly- (3,4- ethylenedioxy -2,5- thiophene) poly styrene sulfonate for they Metal Co., Ltd (Heraeus Precious Metals GmbH&Co.KG, Germany)) coating.PEDOT:PSS is in air In the spin coating from water, toast 10 minutes at 180 DEG C in air then to remove remaining water.By hole transmission layer and shine Layer is applied to the glass plate of these coatings.Hole transmission layer used is crosslinkable.Using the polymer of structure as follows, It can be synthesized according to WO 2010/097155.

HTM polymer

Hole transport polymer is dissolved in toluene.The typical solid content of this solution is that about 5g/l passes through here The thickness degree of the spin coating realization typical 20nm of device.By layer spin coating in inert gas atmosphere (being argon gas in this example), and It is toasted 60 minutes at 180 DEG C.

Luminescent layer is always made of at least two host materials (material of main part, H) and light-emitting dopant (illuminator, D).This Outside, the mixture of a variety of host materials and co-dopant may be present.With such as H1 (40%): H2 (40%): D (20%) form The details provided here means that material H1 exists in luminescent layer with the ratio of 40 weight %, and material H2 is equally with 40 weight % Ratio exist, and dopant D exists with the ratio of 20 weight %.The mixture for being used for luminescent layer is dissolved in toluene or is appointed In selection of land chlorobenzene.The typical solid content of this solution is about 18g/l, here, realizes the typical 60nm's of device by spin coating Thickness degree.By layer spin coating in inert gas atmosphere (being argon gas in this example), and toasted 10 minutes at 160 DEG C.It is used Material be listed in table 10 and table 11, these are all known compound and isomers.

The structural formula of material used in table 10:OLED (without isomers material of the invention)

Apply the material for being used for electron transfer layer by thermal vapor deposition in a vacuum chamber.For example, electron transfer layer can be with It consists of more than one material, the material is mixed with each other with designated volume ratio by coevaporation.With such as ETM1:ETM2 The details that the form of (50%:50%) provides here means that ETM1 and ETM2 material is present in respective 50% volume ratio In the layer.The material used in this example is shown in Table 10.Cathode is formed by thermal evaporation with a thickness of the aluminium layer of 100nm.

Table 11: the structural formula of isomers material

The OLED is characterized in the standard fashion.For this purpose, determining electroluminescence spectrum, it is assumed that the electricity of Lambertian radiation characteristic Stream-voltage-light density feature line (IUL characteristic line) and (work) service life.IUL characteristic line is for determining that parameter is for example specific bright Operating voltage U (being in V) and external quantum efficiency under degree (as unit of %).In 10 000cd/m²Under LD80 be false Determining starting brightness is 10 000cd/m², OLED is reduced to the 80% of initial intensity, that is, is down to 8000cd/m²Service life.

The photoelectric characteristic of a variety of OLED is listed in table 13.Embodiment Comp1 and Comp2 are the mixtures for having isomery pure Comparative example；Embodiment E1 shows the data of the OLED with isomer mixture of the invention.According to the present invention, two kinds it is different Structure body is with identical total concentration with the use of 1:1 mixture.The definite description of material used in EML is found in table 12.

	EML composition
		Comp1	H1 (20%)；H2 (60%)；D_G (20%)
Comp2	H1 (20%)；H3 (60%)；D_G (20%)
		E1	H1 (20%)；H2 (30%)；H3 (30%)；D_G (20%)

Table 12: there is the EML mixture of the different components embodiment of the specification of blending ratio by weight percentage.

Some embodiments are elaborated in detail below, the advantages of to illustrate the compounds of this invention.It is noted, however, that This is only a kind of selection.

Embodiment	In 1000cd/m2Under efficiency	In 8000cd/m2Under LT80 [hour]
			Comp1	75.2cd/A	2200
Comp2	72.9cd/A	1500
			E1	74.2cd/A	1900

Table 13: the work example comprising isomer mixture of the invention

In table 13 it is clear that relative to two comparative examples with the pure EML ink of isomery, there is isomers to stabilize The OLED device of EML ink is in efficiency and tends to be higher than average value in terms of the service life.Therefore, the arithmetic mean of instantaneous value of efficiency is about 74.05cd/A and in 8000cd/m²Under service life LT80 be about 1850 hours.In view of the more high stability of solution of the present invention, As being especially described in detail in table 2 and table 3, therefore mixture of the invention produces unpredictalbe collaboration advantage.Therefore, in OLED Ink is stabilized at all without showing any disadvantage using isomers in device, and tends to lead to improve.

Claims (18)

1. a kind of mixture, it includes at least two organic functions chemical combination object OSM1 of the functional layer that can be used for manufacturing electronic device And OSM2, it is characterised in that compound OSM1 and OSM2 are mutual constitutional isomers.

2. mixture according to claim 1, it is characterised in that can be used for manufacturing described the two of the functional layer of electronic device Kind organic functions chemical combination object OSM1 and OSM2 are selected from fluorescent illuminant, and phosphorescent emitter is shown TADF (hot activation delayed fluorescence) Illuminator, material of main part, electron transport material, exciton-blocking material, electron injection material, hole conductor material, hole note Enter material, n-type dopant, p-type dopant, wide bandgap material, electron-blocking materials and/or hole barrier materials.

3. mixture according to claim 1 or 2, it is characterised in that at least two organic functions chemical combination object OSM1 and OSM2 be selected from fluorenes, indenofluorene, two fluorenes of spiral shell, carbazole, indeno carbazole, indolocarbazole, spiral shell carbazole, pyrimidine, triazine, lactams, three Arylamine, dibenzofurans, dibenzothiophenes, imidazoles, benzimidazole, benzoAzoles, benzothiazole, 5- aryl phenanthridines -6- ketone, 9,10- dehydrogenations are luxuriant and rich with fragrance, fluoranthene, anthracene, benzanthracene, indeno [1,2,3-jk] fluorenes.

4. mixture according to claim 3, it is characterised in that organic functions chemical combination object OSM1 includes at least one function Structural unit and at least one substituent group S1, and organic functions chemical combination object OSM2 is comprising at least one functional architecture unit and extremely A few substituent group S2, wherein the organic functional closes the functional architecture unit and the organic functions chemical combination of object OSM1 The functional architecture unit of object OSM2 is identical.

5. mixture according to claim 4, it is characterised in that substituent group described in the organic functions chemical combination object OSM1 The position of substituent group S2 described in position of the S1 in conjunction with the functional architecture unit and the organic functions chemical combination object OSM2 is not Together.

6. mixture according to claim 4 or 5, it is characterised in that the substitution of the organic functions chemical combination object OSM1 The substituent group S2 of base S1 and the organic functions chemical combination object OSM2 are mutual constitutional isomers.

7. according at least one described mixture in preceding claims 4 to 6, it is characterised in that the functional architecture unit Selected from cavity transmission group, electron transporting groups, material of main part group and broad-band gap group.

8. according at least one described mixture in preceding claims 4 to 7, it is characterised in that the substituent group S1, institute Stating substituent group S2 and/or group B includes solubilized structural unit or crosslinkable groups, preferably comprises solubilized structural unit or cross-linking Group.

9. according at least one described mixture in preceding claims 4 to 8, it is characterised in that the substituent group S1 and institute State substituent group S2 and be selected from phenyl in each case, ortho position, meta or para position xenyl, terphenyl, especially branch three Xenyl, tetrad phenyl, especially branch tetrad phenyl, 1-, 2-, 3- or 4- fluorenyl, 9,9'- diaryl fluorenyls, 1-, 2-, 3- Or two fluorenyl of 4- spiral shell, pyridyl group, pyrimidine radicals, 1-, 2-, 3- or 4- dibenzofuran group, 1-, 2-, 3- or 4- dibenzothiophene, Pyrenyl, triazine radical, imidazole radicals, benzimidazolyl, benzoOxazolyl, benzothiazolyl, 1-, 2-, 3- or 4- carbazyl, 1- or 2- Naphthalene, anthryl, preferably 9- anthryl, trans- and cis- indeno fluorenyl, indeno carbazyl, indolocarbazole base, spiral shell carbazyl, 5- virtue Base-phenanthridines -6- ketone-base, 9,10- dehydrogenation phenanthryl, fluoranthene base, tolyl, mesitylene base, phenoxytoluene base, methyl phenyl ethers anisole base, Triaryl amino, bis- (triaryl amino), three (triaryl amino), hexamethyl indanyl, tetralyl, monocycle alkyl are bicyclic Alkyl, tricyclic alkyl, alkyl, such as tert-butyl, methyl, propyl, alkoxy, alkyl sulfenyl, alkylaryl, triaryl monosilane Base, trialkylsilkl, xanthyl, 10- aryl phenoPiperazine base, phenanthryl and/or terphenyl pitch base, each of described group It can be replaced by one or more groups, but preferably unsubstituted, particularly preferred phenyl, two fluorenes of spiral shell, fluorenes, dibenzofurans, hexichol Bithiophene, anthracene, phenanthrene, terphenyl pitch group.

10. according to one or more mixtures in preceding claims, it is characterised in that described at least two is organic The similarity of functional configuration isomers calculated according to Tanimoto is in the range of 80% to less than 100%.

11. according to one or more mixtures in preceding claims, it is characterised in that described at least two is organic Functional compounds OSM1 and OSM2 is used with the weight rate within the scope of 1:1 to 100:1, preferably 1:1 to 10:1, using having Highest and lowest ratio be each other constitutional isomer the compound ratio.

12. according to one or more mixtures in preceding claims, which is characterized in that in addition to as mutual structure It makes except at least two organic functions chemical combination the object OSM1 and OSM2 of isomers, the mixture also includes at least one glimmering The illuminator of light illuminator, at least one phosphorescent emitter and/or at least one display TADF (hot activation delayed fluorescence), it is described Mixture preferably comprise at least one kind in the form of stereoisomer mixture existing for phosphorescent emitter, preferably have λ and δ isomery Phosphorescent emitter existing for the stereoisomer mixture form of body.

13. the mixture of oligomer, polymer or dendritic macromole, it includes one or more according to claim 1 to 12 Any one of described in constitutional isomer, wherein exist it is one or more from the relative configurations isomers in the mixture to The key of the polymer, oligomer or dendritic macromole, to replace hydrogen atom or substituent group.

14. a kind of composition, it includes it is at least one according to claim 1 in 12 one or more mixtures or The mixture and at least one other chemical combination of oligomer according to claim 13, polymer or dendritic macromole Object, the other compound are selected from fluorescent illuminant, phosphorescent emitter, and display TADF (hot activation delayed fluorescence) shines Body, material of main part, electron transport material, electron injection material, hole conductor material, hole-injecting material, electron-blocking materials And hole barrier materials.

15. a kind of preparation, it includes at least one according to claim 1 to the one or more mixtures or root in 12 According to the mixture of oligomer, polymer or dendritic macromole described in claim 13 or according to claim 14 group Close object and at least one solvent.

16. according to claim 13 oligomeric according to claim 1 to one or more mixtures in 12 Object, the mixture of polymer or dendritic macromole or composition according to claim 14 are in electronic device as master The purposes of body material, hole conductor material or electron transport material.

17. a kind of be used to prepare according to claim 1 to one or more mixtures in 12 or according to claim The method of the mixture of oligomer described in 13, polymer or dendritic macromole, it is characterised in that pass through coupling reaction, preparation Two kinds of structures isomers is simultaneously mixed or is prepared the mixture comprising at least two constitutional isomers.

18. a kind of electronic device, it includes at least one according to claim 1 to one or more mixing in 12 Object, oligomer according to claim 13, the mixture of polymer or dendritic macromole or 4 institute according to claim 1 The composition stated, wherein the electronic device is preferably selected from organic electroluminescence device, organic integrated circuits, organic effect crystalline substance Body pipe, Organic Thin Film Transistors, organic light-emitting transistor, organic solar batteries, organic optical detector, organic photoreception Device, organic field quenching device, light-emitting electrochemical cell and organic laser diode.